A carbohydrate-based approach for the total synthesis of aculeatin D and 6-epi-aculeatin D.
A concise approach for the total synthesis of aculeatin D and 6-epi-aculeatin D employing differentially protected anti, anti-1,3,5-triol alkyne prepared from alpha-D-glucoheptonic-gamma-lactone derivative is documented. Phenol protecting group manipulation for selective O-debenzylation during the hydrogenation of the diyne intermediate and one-pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total synthesis.
Ramana
C V
CV
Division of Organic Chemistry, National Chemical Laboratory, Pune, India. vr.chepuri@ncl.res.in
Srinivas
Burgula
B
D002241:Carbohydrates / Q000737:chemistry*; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C436886:1,7-dioxa-dispiro(5.1.5.2)pentadeca-9,12-dien-11-one; D002241:Carbohydrates; D013141:Spiro Compounds