ISSN:
0170-2041
Keywords:
Hirsutene derivatives
;
Cyclopenta[a]pentalenes
;
Radicals
;
Cyclizations
;
Triquinanes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Radical-Type Cyclization of Dienes, V. - Substrate-Controlled Asymmetric Synthesis of (-)-Hirsutene and (-)-3-Hydroxyhirsutene from (R)-(-)-Carvone(3aR,6aR)-(-)-6a-Methyl-3,3a,4,6a-tetrahydro-2H-cyclopenta- [b]furan-2-one (6) and (1R,4S)-(-)-3-[4-(but-3-inyl)-3-methyl-cyclopent-2-enyl]-2,2-dimethylpropan-1-ol (11) are key compounds in the synthesis reported in this paper. Enantiomerically pure 6 was obtained in five straightforward steps from the inexpensive precursor (R)-(-)-carvone (1). Compound 11 was prepared from 6 via an SN2′ reaction, by analogy with the synthesis reported by Curran et al. The linear triquinanes 13 and 15 were obtained in gram quantities in two additional steps. The utilisation of (S)-(+)-carvone (ent-1) allows access to the other enantiomeric forms. X-ray analysis of 15a confirmed the structure of 15 and, by correlation, that of 13.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930166
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