Synthesis of 24(28)-methylene-1α-hydroxyvitamin D3, a novel vitamin D3 analogue

被引：5

作者：

Guo, Wei ^{[1
]}

Fang, Zhijie ^{[1
]}

Li, Hongliang ^{[1
]}

Liu, Yanan ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China

来源：

JOURNAL OF CHEMICAL RESEARCH | 2014年 / 04期

关键词：

24(28)-methylene-1 alpha-hydroxyvitamin D-3; Wittig-Horner olefination; photoisomerisation; vitamin D-2; KEY INTERMEDIATE; METABOLITE; STEROIDS;

D O I：

10.3184/174751914X13941144023496

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

24(28)-Methylene-1 alpha-hydroxyvitamin D-3 was synthesised in 13 steps from vitamin D-2. The key step of the synthesis involved the Wittig-Horner olefination of a nor-vitamin D-2 aldehyde with diethylphosphono-3-methyl-2-butanone. The resulting enone was followed by reduced methylenation, photoisomerisation and deprotection then gave the target compound.

引用

页码：231 / 235

页数：5

共 24 条

[1] Polyoxygenated sterols from the formosan soft coral Sinularia gibberosa [J].

Ahmed, Atallah F. ;

Hsieh, Ya-Ting ;

Wen, Zhi-Hong ;

Wu, Yang-Chang ;

Sheu, Jyh-Horng .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (09) :1275-1279

[2]

Calverley M. J., 1987, [No title captured], Patent No. [WO8700834A1, 8700834]

[3] SYNTHESIS OF MC-903, A BIOLOGICALLY-ACTIVE VITAMIN-D METABOLITE ANALOG [J].

CALVERLEY, MJ .

TETRAHEDRON, 1987, 43 (20) :4609-4619

[4] SYNTHESIS OF A BIOLOGICALLY-ACTIVE VITAMIN-D2 METABOLITE [J].

CHOUDHRY, SC ;

BELICA, PS ;

COFFEN, DL ;

FOCELLA, A ;

MAEHR, H ;

MANCHAND, PS ;

SERICO, L ;

YANG, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1496-1500

[5] Genomic mechanisms involved in the pleiotropic actions of 1,25-dihydroxyvitamin D-3 [J].

Christakos, S ;

RavalPandya, M ;

Wernyj, RP ;

Yang, W .

BIOCHEMICAL JOURNAL, 1996, 316 :361-371

[6] A stereospecific synthesis of 24(S)-hydroxyvitamin D2, a prodrug for 1α,24(S)-dihydroxyvitamin D2 [J].

Coutts, LD ;

Geiss, WB ;

Gregg, BT ;

Helle, MA ;

King, CHR ;

Itov, Z ;

Mateo, ME ;

Meckler, H ;

Zettler, MW ;

Knutson, JC .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (03) :246-255

[7]

Fuhrhop J., 1994, ORGANIC SYNTHESIS CO, P29

[8]

[郭威 Guo Wei], 2013, [化学试剂, Chemical Reagents], V35, P851

[9]

[郭威 Guo Wei], 2013, [波谱学杂志, Chinese Journal of Magnetic Resonance], V30, P417

[10] STUDIEN IN DER VITAMIN-D-REIHE .24. PHOTO-ISOMERISIERUNG DER TRANS-VITAMINE-D2 UND D3 ZU DEN VITAMINEN-D2 UND D3 [J].

INHOFFEN, HH ;

QUINKERT, G ;

HESS, HJ ;

HIRSCHFELD, H .

CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (11) :2544-2553

← 1 2 3 →