62994-47-2

Usage

InChI:InChI=1/C15H22O3/c1-13(2)7-4-8-14(3)12(13)6-5-11(9-16)15(14,18)10-17/h5,9-10,12,18H,4,6-8H2,1-3H3/t12-,14-,15-/m0/s1

Upstream product

• 82690-92-4 (1S,4aS,8aS)-2-[1,3]Dioxan-2-yl-1-hydroxy-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde 
• 185608-65-5 7-drimen-9α,11,12-triol 
• 34437-62-2 drimendiol 
• 1811-23-0 (+)-confertifoline 
• 514-10-3 (?)-abietic acid 
• 82652-68-4 (4aS,8aS)-5,5,8a-Trimethyl-1-(4-methyl-3-oxo-pentyl)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde 
• 118195-33-8 (4aS,8aS)-2-[1,3]Dioxolan-2-yl-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde 
• 158426-22-3 12-acetoxy-drim-7,9⁽¹¹⁾-diene 
• 156053-25-7 17-acetoxy-7,13E-labdadien-15-ol 
• 161170-33-8 methyl 9α(11)-epoxy-7-drimen-12-oate 
• 161114-71-2 (1R,4aS,8aS)-1-Formyl-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carboxylic acid methyl ester 
• 161114-69-8 methyl 7,9⁽¹¹⁾-drimadien-12-oate 
• 102867-70-9 (1R,4aS,8aS)-5,5,8a-Trimethyl-1-[(E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl]-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carboxylic acid methyl ester 
• 102867-67-4 zamoranic acid methyl ester 

Relevant academic research and scientific papers

Diastereoselective ring - Opening of 12-acetoxy-9α and 9β(11)-epoxy-7-drimene: Homochiral semisynthesis of poligodial and warburganal

Starting from a zamoranic acid derivative (Methyl 15-tetrahydropiranyloxy-7-labden-17-oate) poligodial and warburganal have been synthesized in several steps with a 55% overall yield and 27% overall yield, respectively.

Chemistry of zamoranic acid. Part V. Homochiral semisynthesis of active drimanes: Pereniporin B, polygodial and warburganal

Methyl 14,15-dinor-13-oxo-7-labden-15-oate was obtained from zamoranic acid methyl ester. The former by photochemical cleavage yielded methyl 7,9(11)-drimadien-12-oate, whose chemoselective epoxidation afforded methyl 9α,11-epoxy-7-drimen-12-oate, which is the key synthetic precursor for pereniporin B, polygodial and warburganal.

Terpenoid Precursors via Steroid Degradation: Synthesis of (-)-Warburganal

The sesquiterpene (-)-warburganal was prepared from a (1S)-1-methoxycarbonyl-2,5,5,8a-tetramethyldecahydronaphthalene (4) obtained by degradation of commercial glycyrrhetinic acid.

Synthesis of (-)-Warburganal, an Insect Antifeedant

The enantioselective total synthesis of (-)-warburganal (1) was achieved in 20 steps (8.1percent overall yield) starting from (S)-3-hydroxy-2,2-dimethylcyclohexanone.

The transformation of levopimaric acid into warburganal

The chiral resin acid levopimaric acid (1), isolated from pine oleoresin, is used as a starting material for the synhesis of (-)-warburganal (2).The synthesis proceeds via the endoperoxide of methyl levopimarate, which after ozonolysis, protection of the

A NOVEL PARTIAL SYNTHESIS OF (-)-WARBURGANAL

A short synthesis of (-)-Warburganal, from (+)-confertifoline through the α-epoxide is described.