General strategy for stereoselective synthesis of 1-substituted exo,endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: total synthesis of (+/-)-gmelinol.
[reaction: see text] A general strategy for stereoselective synthesis of 1-substituted exo,endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes including (+/-)-gmelinol from (2,3-trans)-(4,5-cis)-alpha-aroylparaconic esters, which are readily obtained from the reaction of vicinal dianions derived from alpha-aroylsuccinic esters with aromatic aldehydes, is described. The synthetic sequence involves alpha-methylation or alpha-hydroxylation, reduction, bislactonization, and reduction followed by furofuran formation.
Pohmakotr
Manat
M
Department of Chemistry and Center of Protein Structure and Function, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. scmpk@mahidol.ac.th
Pinsa
Attapol
A
Mophuang
Tipwan
T
Tuchinda
Patoomratana
P
Prabpai
Samran
S
Kongsaeree
Palangpon
P
Reutrakul
Vichai
V
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
D001643:Bridged Bicyclo Compounds; D034242:Cyclooctanes; D004952:Esters; C511882:gmelinol