Synthesis and Confirmation of Structure of the Antheridium-Inducing Factor from the Fern Anemia mexicana

Journal of the American Chemical Society

Volumn 110, Issue 12, 1988, Pages 4084-4085

  Furber, Mark ^a   Mander, Lewis N ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000010145     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00220a083     Document Type: Article

References (15)

1. Nakanishi, K.; Endo, M.; Naf, U.; Johnson, L. F. J. Am. Chem. Soc. 1971, 93, 5579–5581. This factor has also been isolated from A. hirsuta (Zanno, P. R.; Endo, M.; Nakanishi, L.; Näf, U.; Stein, C. Naturwissenschaften 1972, 512), A. rotundifolia, and A. flexuosa (Yamane, H.; Nohara, K.; Takahashi, N.; Schraudolf, H. Plant Cell Physiol. 1987, 28, 1203-1207).
2. Corey, E. J.; Myers, A. G. J. Am. Chem. Soc. 1985, 107, 5574–5576. Corey, E. J.; Myers, A. G.; Takahashi, N.; Yamane, H.; Schraudolf, H. Tetrahedron Lett. 1986, 27, 5083–5084.
3. Furber, M.; Mander, L. N. J. Am. Chem. Soc. 1987, 109, 6389–6396.
4. Nester, J. E.; Veysey, S.; Coolbaugh, R. C. Planta 1987, 170, 26–33.
5. Furber, M.; Mander, L. N.; Nester, J. E.; Takahashi, N.; Yamane, H., submitted for publication.
6. This compound was also considered as a candidate for the structure of the less abundant but more potent antheridiogen from Lygodium japoni-cum. Cf. Yamane, H.; Takahashi, N.; Takeno, K.; Furuya, M. Planta 1979, 147, 251–256. Yamane, H.; Satoh, Y.; Nohara, K.; Nakayama, M.; Murofushi, N.; Takahashi, N.; Takeno, K.; Furuya, M.; Furber, M.; Mander, L. N., submitted for publication.
7. Nomenclature and numbering based on the enf-gibberellane skeleton: The Common and Systematic Nomenclature of Cyclic Diterpenes, 3rd revision; Rowe, J. R., Ed., Forest Product Laboratory, U.S. Department of Agriculture: WI, 1968. The location of this group was based on the presence of a peak at m/z 116 in the mass spectrum of the derived trimethyl silyl ether methyl ester (Cf. Kirkwood, P. S.; MacMillan, J. J. Chem. Soc., Perkin Trans. 1, 1982, 689–697) and on the assumption of anisotropic deshielding of H(5) and H(15) in the putative structure.
8. Guindon, Y.; Yoakim, C.; Morton, H. E. J. Org. Chem. 1984, 49, 3912–3920.
9. Cf. Kirkwood, P. S.; MacMillan, J.; Sinnott, M. L. J. Chem. Soc., Perkin Trans 1 1980, 2117–2121.
10. Kirkwood, P. S.; MacMillan, J.; Beale, M. H. J. Chem. Soc., Perkin Trans. 1, 1982, 699–706.
11. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293–4296. The reagent was freshly prepared by stirring the components at 4 °C for 14 h before use.
12. Oshima, K.; Takai, K.; Hotta, H.; Nozaki, H. Tetrahedron Lett. 1978, 2417–2420.
13. 7 methyl ester 3-mesylate, following an earlier study conducted in buffered aqueous acetone (Duri, Z. J.; Hanson, J. R. J. Chem. Soc., Perkin Trans 1 1984, 603–607). Under these conditions we obtained only a 20% yield of the desired 1 β-substitution product, 20% of the 1α-adduct, and 43% of the 3α-isomer. However, the use of the dipolar aprotic solvent HMPT enhanced the yield of the 1 β-isomer considerably; this improvement was readily transferred to the preparation of 13.
14. Bartlett, P. A.; Johnson, W. S. Tetrahedron Lett. 1970, 4459–4462.
15. Naf, W.; Nakanishi, K.; Endo, M. Bot. Rev. 1975, 41, 315–359.