Enantiospecific synthesis of 8-epipuupehedione from (R)-(-)-carvone

被引:37
作者
Maiti, S [1 ]
Sengupta, S [1 ]
Giri, C [1 ]
Achari, B [1 ]
Banerjee, AK [1 ]
机构
[1] Indian Inst Chem Biol, Dept Med Chem, Kolkata 700032, W Bengal, India
关键词
D O I
10.1016/S0040-4039(01)00153-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantiospecific synthesis of the antitumor marine sponge metabolite puupehedione (2a) and its C-8-epimer 2b as their methylenedioxy derivatives 8a and 8b was achieved through concomitant O-allyl deprotection and electrocyolization of 20 derived from (-)-carvone. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:2389 / 2391
页数:3
相关论文
共 14 条
[1]   Total synthesis of both enantiomers of 15-oxopuupehenol methylenedioxy derivatives [J].
Arjona, O ;
Garranzo, M ;
Mahugo, J ;
Maroto, E ;
Plumet, J ;
Saez, B .
TETRAHEDRON LETTERS, 1997, 38 (41) :7249-7252
[2]   Synthesis and antitumor activity of puupehedione and related compounds [J].
Barrero, AF ;
Alvarez-Manzaneda, EJ ;
Chahboun, R ;
Cortés, M ;
Armstrong, V .
TETRAHEDRON, 1999, 55 (52) :15181-15208
[3]   Enantiospecific synthesis of (+)-puupehenone from (-)-sclareol and protocatechualdehyde [J].
Barrero, AF ;
AlvarezManzaneda, EJ ;
Chahboun, R .
TETRAHEDRON LETTERS, 1997, 38 (13) :2325-2328
[4]   Methanol adduct of puupehenone, a biologically active derivative from the marine sponge Hyrtios species [J].
Bourguet-Kondracki, ML ;
Lacombe, F ;
Guyot, M .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (09) :1304-1305
[5]   WIEDENDIOL-A AND WIEDENDIOL-B, CHOLESTERYL ESTER TRANSFER PROTEIN INHIBITORS FROM THE MARINE SPONGE XESTOSPONGLIA-WIEDENMAYERI [J].
COVAL, SJ ;
CONOVER, MA ;
MIERZWA, R ;
KING, A ;
PUAR, MS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (06) :605-610
[6]   SYNTHESIS OF COMPETENT NUCLEOPHILES FOR DELIVERING THE A RING OF TAXOL [J].
DIGRANDI, MJ ;
JUNG, DK ;
KROL, WJ ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4989-4992
[7]  
Faulkner DJ, 1998, NAT PROD REP, V15, P113
[8]   A NEW CHIRAL ROUTE TOWARD TERPENOIDS - ANNULATION OF CARVONE TO TRANS-FUSED AND CIS-FUSED BICYCLIC SYNTHONS [J].
GESSON, JP ;
JACQUESY, JC ;
RENOUX, B .
TETRAHEDRON, 1989, 45 (18) :5853-5866
[9]   BIOGENETICALLY DIVERSE, BIOACTIVE CONSTITUENTS OF A SPONGE, ORDER VERONGIDA - BROMOTYRAMINES AND SESQUITERPENE-SHIKIMATE DERIVED METABOLITES [J].
HAMANN, MT ;
SCHEUER, PJ ;
KELLYBORGES, M .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6565-6569
[10]  
Lova S., 1990, ANTIMICROB AGENTS CH, V34, P2009