Synthesis of A B C-ring subunit of C-nor-D-homo-steroidal alkaloids: towards the total synthesis of cyclopamine.
10.1016/S1875-5364(13)60029-1
- Author:
Xue-Li ZHANG
1
;
Yu-Qi LIAO
;
Peng-Jun CAI
;
He-Quan YAO
;
Ling-Yi KONG
;
Hong-Bin SUN
Author Information
1. Center for Drug Discovery, College of Pharmacy, China Pharmaceutical University, Nanjing, China.
- Publication Type:Journal Article
- MeSH:
Chemistry Techniques, Synthetic;
methods;
Molecular Structure;
Organic Chemistry Phenomena;
Stereoisomerism;
Steroids;
chemistry;
Veratrum Alkaloids;
chemical synthesis;
chemistry
- From:
Chinese Journal of Natural Medicines (English Ed.)
2013;11(3):277-283
- CountryChina
- Language:English
-
Abstract:
A practical approach to the synthesis of the A, B and C-ring subunit of cyclopamine has been developed. This synthetic tactic highlights the utility of mandelate acetal-mediated resolution of the fused ring ketone (±)-4 and IBX-mediated oxidation cascades from 12 to 9. The availability of advanced intermediates from enantiomerically pure (+)-4 and 2 could provide efficient access to biologically active and structurally diverse C-nor-D-homo-steroidal alkaloids such as cyclopamine.
