A concise synthesis of (+)-cassiol

被引:9
作者
Colombo, MI [1 ]
Zinczuk, J [1 ]
Mischne, MP [1 ]
Rúveda, EA [1 ]
机构
[1] Univ Nacl Rosario, CONICET, Inst Quim Organ Sintesis, Fac Ciencias Bioquim & Farmaceut, RA-2000 Rosario, Argentina
关键词
D O I
10.1016/S0957-4166(01)00222-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A synthesis of the anti-ulcerogenic compound (+)-cassiol 1b with 43% overall yield has been achieved. This short and efficient synthesis features the one-pot Julia olefination reaction of lactol (S)-2 with sulfone 3b through the key intermediate (-)-4b. (C) 2001 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1251 / 1253
页数:3
相关论文
共 18 条
[11]  
Momose T, 1999, HETEROCYCLES, V51, P1321
[12]   STRUCTURES OF POTENT ANTIULCEROGENIC COMPOUNDS FROM CINNAMOMUM-CASSIA [J].
SHIRAGA, Y ;
OKANO, K ;
AKIRA, T ;
FUKAYA, C ;
YOKOYAMA, K ;
TANAKA, S ;
FUKUI, H ;
TABATA, M .
TETRAHEDRON, 1988, 44 (15) :4703-4711
[13]   A Synthesis of (+)-Herboxidiene A [J].
Smith, N. D. ;
Kocicnski, P. J. ;
Street, S. D. A. .
Synthesis, 1996, (05)
[14]   Cyclohexonone construction by intramolecular alkylidene C-H insertion: Synthesis of (+)-cassiol [J].
Taber, DF ;
Meagley, RP ;
Doren, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5723-5728
[15]   1ST TOTAL SYNTHESIS OF (+)-CASSIOL - A POTENT ANTIULCEROGENIC COMPOUND [J].
TAKEMOTO, T ;
FUKAYA, C ;
YOKOYAMA, K .
TETRAHEDRON LETTERS, 1989, 30 (06) :723-724
[16]   A new catalyst for a Pd catalyzed alder ene reaction. A total synthesis of (+)-cassiol [J].
Trost, BM ;
Li, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (28) :6625-6633
[17]   CAROTENOIDS AND DEGRADED CAROTENOIDS .7. SYNTHESIS OF (+)-CASSIOL, A POTENT ANTIULCEROGENIC COMPOUND [J].
UNO, T ;
WATANABE, H ;
MORI, K .
TETRAHEDRON, 1990, 46 (16) :5563-5566
[18]   STEREOSELECTIVE SYNTHESIS OF TRISPORIC ACID-A AND ACID-B THEIR METHYL-ESTERS, AND TRISPOROL-A AND TRISPOROL-B, HORMONES AND PROHORMONES OF MUCORACEOUS FUNGI [J].
WHITE, JD ;
TAKABE, K ;
PRISBYLLA, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5233-5244