136611-27-3

Upstream product

• 100-39-0 benzyl bromide 
• 136658-04-3 (-)-4-acetoxy-3-methyl-2-cyclohexen-1-one 
• 57356-79-3 4-hydroxy-3-methyl-cyclohex-2-en-1-one 
• 184481-10-5 1-methyl-7-oxabicyclo<4.1.0>heptan-3-one 
• 57356-77-1 4-acetoxy-3-methyl-2-cyclohexen-1-one 
• 31883-98-4 3-methylcyclohex-3-en-1-one 
• 2873-29-2 D-glucal triacetate 
• 326922-31-0 (S)-3-Benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran 
• 326922-32-1 (S)-6-(benzyloxy)cyclohex-2-en-1-one 
• 326922-30-9 (2S,3S)-2-Iodomethyl-6-methoxy-tetrahydro-pyran-3-ol 
• 23339-17-5 methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside 
• 326922-33-2 (S)-6-Benzyloxy-1-methyl-cyclohex-2-enol 
• 136658-05-4 (S)-4-hydroxy-3-methyl-cyclohex-2-en-1-one 

Downstream Products

• 326922-35-4 (2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one 
• 326922-36-5 (2S,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one 

Relevant academic research and scientific papers

Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene

The practical synthesis of the C-ring precursor of paclitaxel starting from 3-methoxytoluene is described. Lipase-catalyzed kinetic resolution of a substituted cyclohexane-1,2-diol, derived from 3-methoxytoluene in three steps, successfully afforded a desired enantiomer with >99% ee, which was transformed to a cyclohexenone. 1,4-Addition of a vinyl metal species, followed by Mukaiyama aldol reaction with formalin in the presence of a Lewis acid provided the known C-ring precursor of paclitaxel in a 10 g scale.

Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization

A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.

Chiral synthesis of the CD ring unit of paclitaxel from D-glucal

The chiral synthesis of the fully functionalized CD ring unit of paclitaxel 3 is described; the three component coupling reaction of a cyclohexenone derived from D-glucal by way of Ferrier's carbocyclization with vinyl cuprate and formal-dehyde effectivel

Synthesis of optically active cyclohexenol derivatives via enzyme catalyzed ester hydrolysis of 4-acetoxy-3-methyl-2-cyclohexenone

The optically active cyclohexenol derivatives 9a-9d, and 10a-10c are synthesized from (-)-6, which is obtained by enzymatic ester hydrolysis of racemic 8. Attempts towards the synthesis of the taxane skeleton are described.