Asymmetric alkynylzinc additions to aldehydes and ketones

Tetrahedron

Volumn 59, Issue 50, 2003, Pages 9873-9886

  Pu, Lin ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

1,1 binaphthyl; Aldehydes; Alkynylzinc additions; Amino alcohols; Asymmetric; BINOL; Ketones; Propargylic alcohols

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALDEHYDE; ALKALOID; AMINE; AMINOALCOHOL; KETONE; LIGAND; NAPHTHOL DERIVATIVE; NITROGEN; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CANNIZZARO REACTION; CATALYSIS; CATALYST; DERIVATIZATION; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; PRIORITY JOURNAL; ROOM TEMPERATURE; STOICHIOMETRY;

EID: 0242635970     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.042     Document Type: Review

References (81)

1. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
2. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
3. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
4. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
5. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
6. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
7. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
8. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
9. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
10. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
11. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
12. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
13. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
14. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
15. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
16. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
17. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
18. Earlier examples for the use of optically active propargylic alcohols in the synthesis of natural products: (a) Steroids: Johnson W.S., Brinkmeyer R.S., Kapoor V.M., Yarnell T.M. J. Am. Chem. Soc. 99:1977;8341-8343. (b) Prostaglandins: Fried J., Sih J.C. Tetrahedron Lett. 14:1973;3899-3902. (c) Alkaloids: Overman L.E., Bell K.L. J. Am. Chem. Soc. 103:1981;1851-1853. (d) Vitamins E and K Cohen N., Saucy G. J. Org. Chem. 45:1980;582. (e) Palytoxin Leder J., Fijikoa H., Kishi Y. Tetrahedron Lett. 24:1983;1463-1466 (f) Cheon S.H., Christ W.J., Hawkins L.D., Jin H., Kishi Y., Taniguchi M. Tetrahedron Lett. 27:1986;4759-4762. (g) Rovidins and trichoverins: Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776. (h) Cystochalasin: Stork G., Nakamura E. J. Am. Chem. Soc. 105:1983;5510-5512. (i) Dihydromayurone: Lee E., Shin L.J., Kim T.-S. J. Am. Chem. Soc. 112:1990;260-264. (j) Sex pheromones: Vigneron J.P., Bloy V. Tetrahedron Lett. 21:1980;1735-1738 (k) Vigneron J.P., Heiligenmann G. Tetrahedron Lett. 21:1980;2057-2060. (l) Japanese beetle pheromone and dove beetle defense substance: Noyori R., Tomino I., Yamada M., Nishizawa M. J. Am. Chem. Soc. 106:1985;6717. (m) Mosquito oviposition pheromone: Sato T., Gotoh Y., Wakabayashi Y., Fujisawa T. Tetrahedron Lett. 24:1983;4123-4126. (n) Japanese beetle pheromone: Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107-4108 (o) Baker R., Rao V.B. J. Chem. Soc., Perkin Trans. 1. 1:1982;69 (p) Senda S., Mori K. Agric. Biol. Chem. 47:1983;2595. (q) Sesquiterpene: Gibbs R.A., Okamura W.H. J. Am. Chem. Soc. 110:1988;4062-4063. (r) Hydroxyl acids: Midland M.M., Lee P.E. J. Org. Chem. 46:1981;3933-3934.
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