Tetrahedron p. 2267 - 2271 (1974)
Update date:2022-09-26
Topics:
Bellas
Brownlee
Silverstein
The major volatile components of the hairpencil secretion of the male monarch butterfly have been identified as benzyl caproate and either 1, 5, 5, 9-tetramethyl-10-oxabicyclo[4.4.0]-3- decen-2-one(1), or 2, 2, 6, 8-tetramethyl-7-oxabicyclo[4.4.0]-4-decen-3-one(2). One sequence designed to synthesize 1 yielded two isomeric products of structure 1 whose spectra are very similar to each other but distinctly different from those of the natural product; this sequence also yielded a tricyclic ketal (9). A second sequence gave two epimeric spiro compounds (12) and a third sequence gave a [4.3.0] ring system (14).
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Doi:10.1021/ja00365a079
(1982)Doi:10.1021/acs.orglett.9b03471
(2019)Doi:10.1021/ja00368a018
(1982)Doi:10.1007/BF00963403
(1981)Doi:10.1016/S0040-4020(01)97985-2
(1981)Doi:10.1039/b108389a
(2002)