A new synthetic approach to forskolin: Construction of the ABC ring system from D-galactose

被引：15
作者：
Hanna, I
Wlodyka, P
机构：
[1] Lab. de Synt. Organique A., Ecole Polytechnique
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 20期
关键词：
D O I：
10.1021/jo970999h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular Diels-Alder reaction of dienyne 14 afforded naphthopyran 18 which underwent 1,4-addition of methyl copper reagent to give the functionalized tricyclic system of forskolin 17. The synthesis of dienyne 14 is based on a stereoselective introduction of carbon side chains at C(1) and C(2) of tri-O-acetyl-D-galactal via C-Ferrier followed by Claisen-Ireland rearrangements.
引用
收藏
页码：6985 / 6990
页数：6
相关论文
共 48 条
[1]   STUDIES IN THE SYNTHESIS OF A BACCATIN-III STEROID HYBRID - A REMARKABLY RAPID INTRAMOLECULAR DIELS-ALDER REACTION [J].
ALAIMO, CA ;
COBURN, CA ;
DANISHEFSKY, SJ .
TETRAHEDRON LETTERS, 1994, 35 (36) :6603-6606
[2]  
Anies C, 1997, B SOC CHIM FR, V134, P203
[3]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[4]   A SYNTHESIS OF AN ALKYLATED TAXANE MODEL SYSTEM [J].
BONNERT, RV ;
JENKINS, PR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (03) :413-418
[5]   STEREOSELECTIVE REDUCTIVE HYDROXYMETHYLATION OF AN ANNULATED SUGAR DERIVATIVE VIA RADICAL CYCLIZATION [J].
BONNERT, RV ;
DAVIES, MJ ;
HOWARTH, J ;
JENKINS, PR ;
LAWRENCE, NJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (01) :27-29
[6]   Total synthesis of forskolin studies .3. Studies related to an asymmetric synthesis [J].
Calvo, D ;
Port, M ;
Delpech, B ;
Lett, R .
TETRAHEDRON LETTERS, 1996, 37 (07) :1023-1024
[7]  
Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
[8]   SYNTHETIC ROUTES TO FORSKOLIN [J].
COLOMBO, MI ;
ZINCZUK, J ;
RUVEDA, EA .
TETRAHEDRON, 1992, 48 (06) :963-1037
[9]   TOTAL SYNTHESIS OF (+/-)-FORSKOLIN [J].
COREY, EJ ;
JARDINE, PD ;
ROHLOFF, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3672-3673
[10]   STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION [J].
CRAIG, D .
CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) :187-238
12345