TETRAQUINANE DITERPENOIDS - TOTAL SYNTHESIS OF (+ -)-CRINIPELLIN B/

Authors
PIERS E RENAUD J RETTIG SJ
Citation
E. Piers et al., TETRAQUINANE DITERPENOIDS - TOTAL SYNTHESIS OF (+ -)-CRINIPELLIN B/, Synthesis, 1998, pp. 590-602
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Year of publication
1998
Pages
590 - 602
Database
ISI
SICI code
0039-7881(1998):<590:TD-TSO>2.0.ZU;2-5
Abstract
The total synthesis of (+/-)-crinipellin B (4), via a 22-step sequence of reactions starting from 2-methylcyclopent-2-en-1-one (7), is descr ibed. Three distinctly different five-membered annulation sequences (7 --> 11, Scheme 1; 11 --> 15, Scheme 2; 19 --> 30, Scheme 4) played pi votal roles in the synthetic pathway. The constitution and relative co nfiguration of a key synthetic intermediate, compound 32, was confirme d by an X-ray crystallographic study.