Synthetic studies toward merrilactone A: a short synthesis of AB ring motif

被引：21

作者：

Harada, K ^{[1
]}

Kato, H ^{[1
]}

Fukuyama, Y ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Inst Pharmacognosy, Tokushima 7708514, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 43期

关键词：

merrilactone A; regioselective reduction; Stille and Heck reactions; 1,1-dibromo-1-alkene;

D O I：

10.1016/j.tetlet.2005.08.116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to the AB ring motif of merrilactone A has been established by remarkable regioselective reduction of cyclic anhydrides 3 and 8 to the gamma-lactone moiety, followed by the successive Stille and Heck reactions of 1,1-dibromo-l-alkene. (c) 2005 Published by Elsevier Ltd.

引用

页码：7407 / 7410

页数：4

共 19 条

[1] REDUCTION OF CYCLIC ANHYDRIDES WITH NABH4 - VERSATILE LACTONE SYNTHESIS [J].

BAILEY, DM ;

JOHNSON, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) :3574-&

[2] The total synthesis of (±)-merrilactone A [J].

Birman, VB ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (10) :2080-2081

[3] CONTROL OF LITHIUM ALUMINUM HYDRIDE REDUCTION OF CYCLIC DICARBOXYLIC ACID ANHYDRIDES TO PRODUCE GAMMA-LACTONES OR DIOLS [J].

BLOOMFIELD, JJ ;

LEE, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (12) :3919-+

[4] SELECTIVE REDUCTIONS .26. LITHIUM TRIETHYLBOROHYDRIDE AS AN EXCEPTIONALLY POWERFUL AND SELECTIVE REDUCING AGENT IN ORGANIC-SYNTHESIS - EXPLORATION OF THE REACTIONS WITH SELECTED ORGANIC-COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL-GROUPS [J].

BROWN, HC ;

KIM, SC ;

KRISHNAMURTHY, S .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (01) :1-12

[5]

Corey E.J., 1972, TETRAHEDRON LETT, V13, P3769, DOI DOI 10.1016/S0040-4039(01)94157-7

[6] CONCERNING HYDRIDE REDUCTION OF DIELS-ALDER PRODUCTS OF DANISHEFSKYS DIENE [J].

FRASERREID, B ;

RAHMAN, A ;

KELLY, DR ;

SRIVASTAVA, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (10) :1835-1837

[7] Merrilactone A, a novel neurotrophic sesquiterpene dilactone from Illicium merrillianum [J].

Huang, JM ;

Yokoyama, R ;

Yang, CS ;

Fukuyama, Y .

TETRAHEDRON LETTERS, 2000, 41 (32) :6111-6114

[8] Structures of merrilactones B and C, novel anislactone-type sesquiterpenes from Illicium merrillianum, and chemical conversion of anislactone B to merrilactone A [J].

Huang, JM ;

Yang, CS ;

Tanaka, M ;

Fukuyama, Y .

TETRAHEDRON, 2001, 57 (22) :4691-4698

[9] Total synthesis of merrilactone A [J].

Inoue, M ;

Sato, T ;

Hirama, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10772-10773

[10]

KASER MM, 1978, CAN J CHEM, V56, P1524

← 1 2 →