Preparation of 2-hydroxy A-ring precursors for synthesis of vitamin D3 analogues from lyxose

被引：10

作者：

Ibe, Kouta ^{[1
]}

Aoki, Haruko ^{[1
]}

Takagi, Hiromasa ^{[1
]}

Ken-mochi, Kiyohide ^{[1
]}

Hasegawa, Yu-suke ^{[1
]}

Hayashi, Naoto ^{[1
]}

Okamoto, Sentaro ^{[1
]}

机构：

[1] Kanagawa Univ, Dept Mat & Life Chem, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 18期

关键词：

Vitamin D-3 derivatives; A-ring units; Divalent titanium; Enyne metathesis; Catalyzed hydroboration; TI(O-I-PR)(4)/2 I-PRMGX; D-RECEPTOR; BIOLOGICAL-ACTIVITY; ASYMMETRIC-SYNTHESIS; D-3; ANALOGS; REAGENT; ALCOHOLS; DEOXYGENATION; DERIVATIVES; METATHESIS;

D O I：

10.1016/j.tetlet.2015.03.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of vitamin D-3 (VD3) A-ring precursors 1b, 2, and 3, which are precursors for 2-hydroxy or 2-alkoxy 1 alpha-OH-VDs, via a common intermediate enyne 1a were carried out starting from lyxose. From 1a, exo-methylene halide 2, which is an A-ring intermediate for the synthesis of 2-alkoxy vitamin D3, was synthesized by a Ti(II)-mediated cyclization. Phosphine oxide 3a and benzothiazolylsulfone 3b, which are 19-nor-type A-ring intermediates of 2-alkoxy vitamin D, were prepared by a Ru-catalyzed metathesis followed by a Ni-catalyzed 1,4-selective hydroboration reaction. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2315 / 2318

页数：4

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