Calciferol and its relatives. Part 22. A direct total synthesis of vitamin D2 and vitamin D3
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 590-595
- https://doi.org/10.1039/p19780000590
Abstract
Direct total syntheses are described of 3-deoxyvitamin D2, vitamin D2, and vitamin D3. For the first, the lithio-derivative of (Z)-2-(2-methylenecyclohexylidene)ethyl(diphenyl)phosphine oxide and the Windaus–Grundmann ketone C19H32O were the reacting partners; for the second, the same ketone and the lithio-derivative of a protected form of (S)-(Z)-2-(5-hydroxy-2-methylenecyclohexylidene)ethyl(diphenyl)Phosphine oxide; and for the third, the same lithio-derivative and des-AB-cholestan-8-one. In these reactions, the original Z-allyl geometry of the phosphine oxides was completely preserved in the 5,6-double bond of the products, and the new (7,8-) double bond was formed with exclusive E-geometry.This publication has 1 reference indexed in Scilit:
- Calciferol and its relatives. Part 20. A synthesis of Windaus and Grundmann's C19 ketoneJournal of the Chemical Society, Perkin Transactions 1, 1977