THERMOCONVERSION OF CARYOPHYLLENE- TO FARNESENE-TYPE SESQUITERPENES -SHORT ACCESS TO THE ENANTIOMERS OF (6RS,7RS)-6,7-EPOXY-6,7-DIHYDRO-BETA-FARNESENES AND (6RS,7SR)-6,7-EPOXY-6,7-DIHYDRO-BETA-FARNESENES

Authors
GIERSCH WK BOSCHUNG AF SNOWDEN RL SCHULTEELTE KH
Citation
Wk. Giersch et al., THERMOCONVERSION OF CARYOPHYLLENE- TO FARNESENE-TYPE SESQUITERPENES -SHORT ACCESS TO THE ENANTIOMERS OF (6RS,7RS)-6,7-EPOXY-6,7-DIHYDRO-BETA-FARNESENES AND (6RS,7SR)-6,7-EPOXY-6,7-DIHYDRO-BETA-FARNESENES, Helvetica Chimica Acta, 77(1), 1994, pp. 36-40
Citations number
24
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
77
Issue
1
Year of publication
1994
Pages
36 - 40
Database
ISI
SICI code
0018-019X(1994)77:1<36:TOCTFS>2.0.ZU;2-Y
Abstract
Flash-vacuum thermolysis of the four diastereoisomeric 5,6-epoxy-5,6-d ihydro-caryophyllenes 1-4 at 500-550 degrees/0.1-0.7 Torr leads to the hitherto unreported enantiomers of (6RS,7RS)- and (6RS,7SR)-6,7-epoxy -6,7-dihydro-beta-farnesenes ((+/-)-5 and (+/-)-6, resp.). In particul ar, (+)-5 is formed in 45% yield (ca. 90% ee) and is, thus, an attract ive chiral building block for natural-product synthesis.