A TOTAL SYNTHESIS OF THE SESQUITERPENE QUINONE METACHROMIN-A

被引:26
作者
ALMEIDA, WP
CORREIA, CRD
机构
[1] UNIV FED RIO DE JANEIRO,INST QUIM,BR-21945970 RIO JANEIRO,BRAZIL
[2] UNIV ESTADUAL CAMPINAS,INST QUIM,BR-13081970 CAMPINAS,SP,BRAZIL
关键词
D O I
10.1016/S0040-4039(00)76220-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of the marine natural product metachromin A was accomplished through a convergent synthesis amenable to the preparation of synthetic analogues. The main features of this synthesis are the introduction of the oxygenation at C-17 employing a Thiele acetoxylation reaction and a stereoselective Horner-Wadsworth-Emmons coupling
引用
收藏
页码:1367 / 1370
页数:4
相关论文
共 23 条
[1]  
[Anonymous], 1977, WILEY ONLINE LIB
[2]  
BACHMANN WE, 1942, ORG REACTIONS, V1, P38, DOI DOI 10.1002/0471264180.OR001.02
[3]   THE MICHAELIS-ARBUZOV REARRANGEMENT [J].
BHATTACHARYA, AK ;
THYAGARAJAN, G .
CHEMICAL REVIEWS, 1981, 81 (04) :415-430
[4]   OLEFIN SYNTHESIS WITH ORGANIC PHOSPHONATE CARBANIONS [J].
BOUTAGY, J ;
THOMAS, R .
CHEMICAL REVIEWS, 1974, 74 (01) :87-99
[5]   STEREOSPECIFIC TOTAL SYNTHESIS OF GIBBERELLIC-ACID - KEY TRICYCLIC INTERMEDIATE [J].
COREY, EJ ;
DANHEISER, RL ;
CHANDRASEKARAN, S ;
SIRET, P ;
KECK, GE ;
GRAS, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (25) :8031-8034
[6]   LEWIS ACID-CATALYZED MICHAEL-TYPE ADDITION - A NEW REGIOSELECTIVE AND DIASTEREOSELECTIVE ANNULATION METHOD USING METHYL VINYL KETONE [J].
DUHAMEL, P ;
DUJARDIN, G ;
HENNEQUIN, L ;
POIRIER, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (03) :387-396
[7]  
FAULKNER D, 1991, J NAT PROD REP, V8, P116
[8]  
FAULKNER D, 1990, J NAT PROD REP, V7, P282
[9]  
FAULKNER D, 1992, J NAT PROD REP, V9, P338
[10]   MARINE NATURAL-PRODUCTS [J].
FAULKNER, DJ .
NATURAL PRODUCT REPORTS, 1992, 9 (04) :323-364