Synthesis of (±)-podorhizone via intermediate α-hydroxyalkylation of a β-benzyl γ-butyrolactone
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 13,p. 556-557
- https://doi.org/10.1039/c39780000556
Abstract
α-Hydroxyalkylation of β-(3,4-methylenedioxybenzyl)-γ-butyrolactone (1) with 3,4,5-trimethoxybenzaldehyde, using lithium hexamethyldisilylamide as a base, affords a 1 : 1 mixture of (±)-podorhizol (4) and (±)-epipodorhizol (5); Jones's oxidation of this mixture gives (±)-podorhizone (6) in 63% overall yield.This publication has 2 references indexed in Scilit:
- Synthetic studies on lignan lactones: aryl dithiane route to (.+-.)-podorhizol and (.+-.)-isopodophyllotoxone and approaches to the stegane skeletonThe Journal of Organic Chemistry, 1978
- Podophyllum‐ Lignane: Struktur und Absolutkonfiguration von Podorhizol‐β‐D‐glucosid ( = Lignan F). 19. Mitt. über mitosehemmende Naturstoffe [1]Helvetica Chimica Acta, 1967