New total synthesis of (+)-ambrein

被引：19

作者：

Fujiwara, Naoko ^{[1
]}

Kinoshita, Masako ^{[1
]}

Akita, Hiroyuki ^{[1
]}

机构：

[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 21期

关键词：

D O I：

10.1016/j.tetasy.2006.11.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3037 / 3045

页数：9

共 8 条

[1]

Baoyu M., 2001, ORG LETT, V3, P1491

[2] The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].

Blakemore, PR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585

[3]

Blakemore PR, 1999, SYNTHESIS-STUTTGART, P1209

[4] Chemoenzymatic synthesis of (S)- and (R)-γ-cyclogeraniols [J].

Fujiwara, Naoko ;

Kinoshita, Masako ;

Akita, Hiroyuki .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2006, 40 (1-2) :64-72

[5] Total synthesis of (-)-(8R, 10S)- and (+)-(8S, 10R)-8-hydroxypolypoda-13,17,21-triene based on enzymatic resolution [J].

Kinoshita, M ;

Nakamura, D ;

Fujiwara, N ;

Akita, H .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2003, 22 (3-4) :161-172

[6]

MORI K, 1990, LIEBIGS ANN CHEM, P361

[7]

Ohloff G., 1982, FRAGRANCE CHEM, P535, DOI DOI 10.1016/B978-0-12-685850-1.50020-6

[8] Synthesis of (+)-Ambrein [J].

Tanimoto, H ;

Oritani, T .

TETRAHEDRON, 1997, 53 (10) :3527-3536

← 1 →