Synthesis of the angiotensin-converting enzyme inhibitor (±)-A58365A

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2519-2522

  Clive, Derrick L J ^a   Coltart, Don M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3 CARBOXY 1,2,3,5 TETRAHYDRO 8 HYDROXY 5 OXO 6 INDOLIZIDINEPROPIONIC ACID; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; LACTONE DERIVATIVE; PYRIDONE DERIVATIVE; SPIRO COMPOUND; TIN DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHROMATOGRAPHY; CRYSTALLIZATION; CYCLIZATION; DRUG ISOLATION; DRUG PURIFICATION; DRUG SYNTHESIS; FERMENTATION; STREPTOMYCES; X RAY ANALYSIS;

STREPTOMYCES;

EID: 0032560045     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00384-0     Document Type: Article

References (17)

1. 1 Hunt, A.H.; Mynderse, J.S.; Samlaska, S.K.; Fukuda, D.S.; Maciak, G.M.; Kirst, H.A.; Occolowitz, J.L.; Swartendruber, J.K.; Jones, N.D. J. Antibiotics 1988, 41, 171, and references therein.
2. 2 Clive, D.L.J.; Zhou, Y.; de Lima, D.P. J. Chem. Soc., Chem. Commun. 1996, 1463.
3. 3 Prior syntheses of optically pure 1: Fang, F.G; Danishefsky, S.J. Tetrahedron Lett. 1989, 30, 3621. Wong, P.L; Moeller, K.D. J. Am. Chem. Soc. 1993, 115, 11434.
4. 3 Prior syntheses of optically pure 1: Fang, F.G; Danishefsky, S.J. Tetrahedron Lett. 1989, 30, 3621. Wong, P.L; Moeller, K.D. J. Am. Chem. Soc. 1993, 115, 11434.
5. 4 For an example of 6-exo trigonal closure onto an enamide double bond, see: Yuasa, Y.; Kano, S.; Shibuya, S. Heterocycles 1991, 32, 2311.
6. 5 Non-systematic numbering is used.
7. 3 used in this experiment should be purified by the method of reference 7.
8. 7 Calder, A.; Forrester, A.R.; Thomson, R.H. J. Chem. Soc. (C) 1969, 514.
9. 8 Although the synthesis of optically pure 7 (by the corresponding route to that shown in Scheme 2) has been reported (reference 9), considerable experimentation was needed in order to develop a reliable and efficient (>85%) method for making the organozinc (in our racemic series). A procedure for converting optically pure 8 into 10 has been described (reference 9), but we obtained far better results by using a different method for activating the zinc (Fisher Certified Zinc Metal Dust, Z-5). Activation was done under the conditions specified in reference 10, but using the proportions given in reference 11.
10. 9 Dunn, M.J.; Jackson, R.F.W. J. Chem. Soc., Chem. Commun. 1992, 319.
11. 10 Yeh, M.C.P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799.
12. 11 Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Wishart, N.; Ellis, D.; Wythes, M. Synlett 1993, 499.
13. 12 EDCI = 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochioride; HOBT = 1-hydroxybenzotriazole hydrate.
14. 13 The Lemieux-Johnson procedure gave, in this instance, poorer yields.
15. 14 Cyclization to 6-membered enamides appears to be easier than for the 5-membered series: Cf. Robl, J.A. Tetrahedron Lett. 1994, 35, 393. Ojima, I.; Tzamarioudaki, M.; Eguchi, M. J. Org. Chem. 1995, 60, 7078.
16. 14 Cyclization to 6-membered enamides appears to be easier than for the 5-membered series: Cf. Robl, J.A. Tetrahedron Lett. 1994, 35, 393. Ojima, I.; Tzamarioudaki, M.; Eguchi, M. J. Org. Chem. 1995, 60, 7078.
17. 15 Cf. Paterson I.; Cowden, C.; Watson, C. Synlett 1996, 209.