An efficient asymmetric synthesis of 1α,25-(OH)2 vitamin D3 A-ring synthon

Kazuo Nagasawa, Hideki Ishihara, Yoshiro Zako, Isao Shimizu

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Abstract

Chiral synthesis of the A-ring synthon 3 of 1α,25-dihydroxyvitamin D3 (1a) based on palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates is described. Reaction of (E)-4b and (Z)-4d in the presence of Pd(OAc)2, PPh3, and K2CO3 gave (E)-3b and (Z)-3d, respectively. Optically active 4d was prepared from 24 by asymmetric aldol reaction using 31, which was cyclized to 3d. With further reactions, 1α,25-dihydroxyvitamin D3 (1a) was obtained.

Original languageEnglish
Pages (from-to)2523-2529
Number of pages7
JournalJournal of Organic Chemistry
Volume58
Issue number9
Publication statusPublished - 1993

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Calcitriol
Cholecalciferol
Cyclization
Palladium
palladium(II) acetate
3-hydroxybutanal
potassium carbonate

ASJC Scopus subject areas

  • Organic Chemistry

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Nagasawa, K., Ishihara, H., Zako, Y., & Shimizu, I. (1993). An efficient asymmetric synthesis of 1α,25-(OH)2 vitamin D3 A-ring synthon. Journal of Organic Chemistry, 58(9), 2523-2529.

An efficient asymmetric synthesis of 1α,25-(OH)2 vitamin D3 A-ring synthon. / Nagasawa, Kazuo; Ishihara, Hideki; Zako, Yoshiro; Shimizu, Isao.

In: Journal of Organic Chemistry, Vol. 58, No. 9, 1993, p. 2523-2529.

Research output: Contribution to journalArticle

Nagasawa, K, Ishihara, H, Zako, Y & Shimizu, I 1993, 'An efficient asymmetric synthesis of 1α,25-(OH)2 vitamin D3 A-ring synthon', Journal of Organic Chemistry, vol. 58, no. 9, pp. 2523-2529.
Nagasawa, Kazuo ; Ishihara, Hideki ; Zako, Yoshiro ; Shimizu, Isao. / An efficient asymmetric synthesis of 1α,25-(OH)2 vitamin D3 A-ring synthon. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 9. pp. 2523-2529.
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