ISSN:
0170-2041
Keywords:
(-)-Coriolin
;
(-)-Epicoriolin
;
Radicals
;
Cyclization
;
Triquinans
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Radical-Type Cyclization of Dines, VI. - Total Synthesis of (-)-Coriolin and (-)-Epicoriolin from (S)-(+)-Carvone(3aR,4S,6aS)-(+)-4-(4-Methoxybenzyloxy)-6a-methyl-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (10) and (3aR,3bR,4R,6aS,7S,7aS)-(-)-decahydro-4,7-dihydroxy-3a,5,5-trimethyl-3-methylene-2H-cyclopenta[a]pentalen-2-one (21) are the key intermediates in the synthesis of the title compounds 1 and 1a. Enantiomerically pure 10 is produced from (S)-(+)-carvone (4) in seven straightforward reactions. Compound 21 is produced from 10 by analogy with the method developed for the synthesis of (-)-hirsutene. Through the introduction of the double bond into 21 via the silylenolether 23 one arrives at precoriolin 25, which is converted into (-)-coriolin (1) and the C-3 epimer (-)-epicoriolin (1a) (63:37) with hydrogen peroxide. The structures of 1 and 1a were confirmed via X-ray crystallography.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1993199301181
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