THE CD-EXCITON CHIRALITY METHOD AND BENZOYLATION OF STERICALLY HINDERED ALPHA-GLYCOL BY TRANSESTERIFICATION - FORSKOLIN CASE

Authors
SUGIOKA T HARADA N EHARA H SOUTOME T KURIKI T
Citation
T. Sugioka et al., THE CD-EXCITON CHIRALITY METHOD AND BENZOYLATION OF STERICALLY HINDERED ALPHA-GLYCOL BY TRANSESTERIFICATION - FORSKOLIN CASE, Enantiomer, 2(2), 1997, pp. 117-121
Citations number
5
Categorie Soggetti
Chemistry,"Chemistry Inorganic & Nuclear",Biology
Journal title
Enantiomer → ACNP
ISSN journal
10242430
Volume
2
Issue
2
Year of publication
1997
Pages
117 - 121
Database
ISI
SICI code
1024-2430(1997)2:2<117:TCCMAB>2.0.ZU;2-C
Abstract
The sterically hindered hydroxyl group at the 6-position of 7-deacetyl forskolin (2) was benzoylated by a trans-esterification reaction of 7 beta-p-bromobenzoate (3), yielding 6 beta-p-bromobenzoate (5), from wh ich 6 beta,7 beta-bis(p-bromobenzoate) (6) was prepared. The CD spectr um of 6 showed typical exciton split Cotton effects of positive excito n chirality establishing the absolute stereochemistry of forskolin (1) and its family compounds. The additivity rule of CD exciton Cotton ef fects was confirmed in the case of forskolin derivatives.