Biogenetic syntheses of kopsijasminilam and deoxykopsijasminilam

Citation
Me. Kuehne et al., Biogenetic syntheses of kopsijasminilam and deoxykopsijasminilam, J ORG CHEM, 65(20), 2000, pp. 6434-6440
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
20
Year of publication
2000
Pages
6434 - 6440
Database
ISI
SICI code
0022-3263(20001006)65:20<6434:BSOKAD>2.0.ZU;2-A
Abstract
The hexacyclic ketoester 7, derived from cyclization of racemic minovincine (6), was reduced to two C-19 epimeric alcohols 8 and 9. Stereoelectronical ly controlled fragmentations of corresponding O-sulfonyl derivatives provid ed, respectively, the hexacyclic enamine 14 and, after oxidation of the ole fin 16, the pentacyclic lactam 17 with a brigehead double bond. Formation o f a carbamate, introduction of a second double bond at C-16, and conjugate reductive hydroxylation at C-20, or hydrogenation, gave the title products.