135854-66-9

Basic information

• Product Name: 14-oxopodocarpa-8⁽⁹⁾-ene
• CAS NO: 135854-66-9
• Molecular Weight: 246.393
• Mol File: 135854-66-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 14-oxopodocarpa-8⁽⁹⁾-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 14-oxopodocarpa-8⁽⁹⁾-ene(135854-66-9)
• EPA Substance Registry System: 14-oxopodocarpa-8⁽⁹⁾-ene(135854-66-9)

Safety Data

• Hazardous Substances Data: 135854-66-9(Hazardous Substances Data)

Upstream product

• 5720-79-6 (+/-)-14-methoxypodocarpa-8,11,13-triene 

Downstream Products

• 69903-86-2 (+/-)-veadeiroic acid 
• 69940-49-4 (+/-)-veadeirol 

Relevant articles and documents

Birch reduction of 14-methoxypodocarpa-8,11,13-triene and a stereoselective synthesis of veadeiroic acid and veadeirol - Two novel diterpenes with cleistanthane skeleton

14-Methoxypodocarpa-8,11,13-triene (1) has been reduced by Li in liquid NH3, using EtOH-t-BuOH with THF as cosolvent to 14-oxopodocarpa-8(9)-ene (5) as the major product.This is converted successively into a keto-acetal (6), a dihydrobenzaldehyde (8), and an aromatic aldehyde (9) through more or less standard reactions.The aldehyde (9) is oxidised to (+/-)-veadeiroic acid (2a) and reduced to (+/-)-veadeirol (2b) thus effecting the first total synthesis of these two naturally occurring diterpenes with rare cleistanthane skeleton.