SYNTHESIS OF (1-ALPHA,7-ALPHA,8-BETA)-(+ -)-8-METHYL-2-METHYLENEBICYCLO[5.3.0]DEC-5-EN-8-OL - STRUCTURE REVISION OF NATURAL DICTAMNOL/

Authors
PIET DP ORRU RVA JENNISKENS LHD VANDEHAAR C VANBEEK TA FRANSSEN MCR WIJNBERG JBPA DEGROOT A
Citation
Dp. Piet et al., SYNTHESIS OF (1-ALPHA,7-ALPHA,8-BETA)-(+ -)-8-METHYL-2-METHYLENEBICYCLO[5.3.0]DEC-5-EN-8-OL - STRUCTURE REVISION OF NATURAL DICTAMNOL/, Chemical and Pharmaceutical Bulletin, 44(7), 1996, pp. 1400-1403
Citations number
17
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
44
Issue
7
Year of publication
1996
Pages
1400 - 1403
Database
ISI
SICI code
0009-2363(1996)44:7<1400:SO(->2.0.ZU;2-S
Abstract
The total synthesis of the title compound (+/-)-1 is described, The ke y step in the synthesis of this cis-fused trinor-guaiane is the base-i nduced and -directed rearrangement of the tosylate ester 4. Because of differences in the spectral data of synthetic (+/-)-1 and natural dic tamnol, a trinor-guaiane isolated from Dictamnus dasycarpus TURCZ., a revised structure for the natural product is proposed, Nuclear Overhau ser effect (NOE) difference experiments and a detailed investigation o f the air-induced cyclization reaction of pregeijerene, isolated from Amyris diatrypa SPRENGEL, support the structure revision of natural di ctamnol.