Asymmetric synthesis of the (2S,4S,6S)-2,4,6-trimethylnonyl subunit of siphonarienes

被引：0

作者：

Díaz, DD ^{[1
]}

Crisóstomo, FRP ^{[1
]}

Martín, VS ^{[1
]}

机构：

[1] Univ La Laguna, Inst Univ Bioorg Antonio Gonzalez, San Cristobal la Laguna 38206, Tenerife, Spain

来源：

ISRAEL JOURNAL OF CHEMISTRY | 2001年 / 41卷 / 04期

关键词：

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The paper describes an asymmetric approach to the synthesis of the (2S,4S,6S)-2,4,6-trimethylnonyl segment of siphonarienes. The key step used is a newly developed methodology to obtain sec-dialkyl acetylenes based on the intramolecular hydride transfer from a secondary gamma-benzyloxy group with well-defined absolute stereochemistry, ensured by a Sharpless asymmetric epoxidation reaction, to a cation generated by Lewis acid treatment of a tertiary Co-2(CO)(6)-complexed propargylic alcohol.

引用

页码：297 / 302

页数：6

共 50 条

[1] Enantioselective synthesis of (+)-(2S,4S,6S)-1-ethoxycarbonyl-6-hydroxymethyl-4-methylpipecolate
Acherki, H
Alvarez-Ibarra, C
Guzmán-Fernández, S
Quiroga-Feijóo, ML
TETRAHEDRON-ASYMMETRY, 2004, 15 (04) : 693 - 697
[2] Asymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine
Lépine, R
Carbonnelle, AC
Zhu, JP
SYNLETT, 2003, (10) : 1455 - 1458
[3] Stereospecific synthesis of (2S,4S,6S)-2-amino-4,6-dihydroxypimelic acid
Mehlfuhrer, M
Thirring, K
Berner, H
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12): : 4078 - 4081
[4] Asymmetric total synthesis of (1S,2S,4S)-β-elemene
Chen, Wei
Feng, Zhun
Liu, Qiang
RSC ADVANCES, 2022, 12 (13) : 8249 - 8255
[5] SYNTHESIS OF (2S,4S,6S)-2-AMINO-6-HYDROXY-4-METHYL-8-OXODECANOIC ACID AND (4S,E)-4-METHYLHEX-2-ENOIC ACID CONSTITUENTS OF LEUCINOSTATINES
ELHADRAMI, M
LAVERGNE, JP
VIALLEFONT, P
ITTO, MYA
HASNAOUI, A
TETRAHEDRON LETTERS, 1991, 32 (32) : 3985 - 3988
[6] A CONVENIENT SYNTHESIS OF (2S,4S)-4-HYDROXYPROLINE
SEKI, M
MATSUMOTO, K
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (06) : 1161 - 1162
[7] Towards a total synthesis of ustiloxins A & B. Stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline
Hutton, CA
White, JM
TETRAHEDRON LETTERS, 1997, 38 (09) : 1643 - 1646
[8] Stereoselective synthesis of fully protected (2S,4S,6S)-2-amino-6-hydroxy-4-methyl-8-oxodecanoic acid (AHMOD)
Zhang, Wei
Li, Xiangpeng
Ding, Ning
Li, Yingxia
JOURNAL OF PEPTIDE SCIENCE, 2012, 18 (03) : 163 - 169
[9] A concise synthesis of (2S,4R)- and (2S,4S)-4-methylglutamic acid
Gu, ZQ
Li, M
TETRAHEDRON LETTERS, 2003, 44 (15) : 3203 - 3205
[10] Synthesis of (2S,4S)- and (2S,4R)-5-fluoroleucine and (2S,4S)-[5,5-2H2]-5-fluoroleucine
Charrier, JD
Hadfield, DS
Hitchcock, PB
Young, DW
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (04) : 474 - 482

← 1 2 3 4 5 →