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

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 09期

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

页码：1251 / 1253

页数：3

共 18 条

[1] Enantioselective syntheses and resolution of the key white intermediate for the synthesis of trisporic acids [J].

Bacigaluppo, JA ;

Colombo, MI ;

Preite, MD ;

Zinczuk, J ;

Ruveda, EA ;

Sieler, J .

TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1041-1057

[2] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES [J].

BAUDIN, JB ;

HAREAU, G ;

JULIA, SA ;

RUEL, O .

TETRAHEDRON LETTERS, 1991, 32 (09) :1175-1178

[3]

BILLINGTON R, 1996, SYNTHESIS-STUTTGART, P285

[4] Toward the development of a general chiral auxiliary .5. High diastereofacial selectivity in cycloadditions with trienol silyl ethers: An application to an enantioselective synthesis of (-)-cassioside [J].

Boeckman, RK ;

Liu, YG .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7984-7985

[5] Studies directed toward the preparation of key intermediates for the synthesis of trisporic acids and cassiol [J].

Colombo, MI ;

Zinczuk, J ;

Mischne, MP ;

Rúveda, EA .

PURE AND APPLIED CHEMISTRY, 2001, 73 (03) :623-626

[6] DEMONSTRATION OF THE SYNTHETIC POWER OF OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE DIELS-ALDER REACTIONS BY VERY EFFICIENT ROUTES TO CASSIOL AND GIBBERELLIC-ACID [J].

COREY, EJ ;

GUZMANPEREZ, A ;

LOH, TP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3611-3612

[7] An enantioselective total synthesis of (+)-cassiol [J].

Irie, O ;

Fujiwara, Y ;

Nemoto, H ;

Shishido, K .

TETRAHEDRON LETTERS, 1996, 37 (51) :9229-9232

[8]

Maiti S, 1998, SYNLETT, P129

[9]

Maria AOM, 2000, BIOL PHARM BULL, V23, P555

[10] Synthesis of optically active 3-alkoxy-6-hydroxymethyl-6-methyl-2-cyclohexenone [J].

Miyaoka, H ;

Kajiwara, Y ;

Hara, M ;

Suma, A ;

Yamada, Y .

TETRAHEDRON-ASYMMETRY, 1999, 10 (16) :3189-3196

← 1 2 →