A straightforward strategy toward the construction of polypropionate frameworks, based on a sequence of diastereloselective Lewis acid-mediated aldol reaction and diastereoselective radical debromination reaction

被引：8

作者：

Kiyooka, S ^{[1
]}

Shiinoki, M

Nakata, K

Goto, F

机构：

[1] Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan

[2] Kochi Univ, Dept Chem, Akebono, Kochi 7808520, Japan

[3] Otsuka Pharmaceut Co Ltd, Cellular Technol Inst, Kawauchi, Tokushima 7710130, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(02)01074-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach joining highly diastereoselective Mukaiyama aldol reaction (process A) to the following radical debromination reaction (process B) provides a reliable way to the stereoselective divergent synthesis of polypropionate frameworks. A practical and reliable synthesis of the complete set of propionate stereotetrads from enantiopure syn- and anti-2-methyl-3-methoxy-3-phenylpropanals was achieved by using the straightforward strategy. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5377 / 5380

页数：4

共 8 条

[1] Diastereoselective radical debromination approach toward divergent syntheses of syn- and anti-propionate units, coupled with enantioselective and/or diastereoselective Lewis acid-promoted aldol reactions
Kiyooka, S
TETRAHEDRON-ASYMMETRY, 2003, 14 (19) : 2897 - 2910
[2] Carbohydrate-Based Strategy for the Synthesis of Zaragozic Acid via a Novel Lewis Acid-Mediated Reaction of an a-Acetoxy Sulfide
Kraus, G. A.
Maeda, H.
Journal of Organic Chemistry, 1995, 60 (01):
[3] CARBOHYDRATE-BASED STRATEGY FOR THE SYNTHESIS OF ZARAGOZIC ACID VIA A NOVEL LEWIS ACID-MEDIATED REACTION OF AN ALPHA-ACETOXY SULFIDE
KRAUS, GA
MAEDA, H
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01): : 2 - 3
[4] DIASTEREOSELECTIVE SYNTHESIS OF BETA-AMINO ESTERS BY THE LEWIS ACID-MEDIATED REACTION OF N-TOSYL ALDIMINES WITH KETENE BIS(TRIMETHYLSILYL) ACETALS
SHIMADA, S
SAIGO, K
ABE, M
SUDO, A
HASEGAWA, M
CHEMISTRY LETTERS, 1992, (08) : 1445 - 1448
[5] REINVESTIGATION OF THE LEWIS ACID-MEDIATED REACTION OF 3-ARYL-SUBSTITUTED ALLYLTIN REAGENTS TOWARD ALDEHYDES - DIVERGENT STEREOCONTROL OF THE PRODUCT BY LEWIS-ACIDS
NISHIGAICHI, Y
TAKUWA, A
CHEMISTRY LETTERS, 1994, (08) : 1429 - 1432
[6] LEWIS-ACID-MEDIATED AND CATIONIC LITHIUM-MEDIATED DIASTEREOSELECTIVE ALDOL-TYPE REACTION-BASED ON A DOUBLE CHIRAL RECOGNITION MANNER FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED SERINES
SANO, S
LIU, XK
TAKEBAYASHI, M
KOBAYASHI, Y
TABATA, K
SHIRO, M
NAGAO, Y
TETRAHEDRON LETTERS, 1995, 36 (23) : 4101 - 4104
[7] Toward a Combined Molecular Dynamics and Quantum Mechanical Approach to Understanding Solvent Effects on Chemical Processes in the Pharmaceutical Industry: The Case of a Lewis Acid-Mediated SNAr Reaction
Iyemperumal, Satish Kumar
Lee, Elaine C.
Tanoury, Gerald J.
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2023, 27 (04) : 742 - 754
[8] Enhanced reactivity and anti selectivity in the asymmetric Lewis acid-mediated Mukaiyama aldol reaction of alpha-alkoxythiolketene acetals with alpha,beta-disubstituted enals: synthesis of the C26-C33 segment of rapamycin
White, JD
Deerberg, J
CHEMICAL COMMUNICATIONS, 1997, (19) : 1919 - 1920

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