Abstract
A diastereocontrolled route to the naturally occurring heptiol, perseitol (D-glycero-D-galactoheptiol) isolated as a complex with K ion from leaves of Scurrula fusca (Loranthaceae), has been developed starting from a chiral building block containing a 7,8-dioxabicyclo[3.2.1]octane framework.
Highlights
The leaves of a parasitic plant Scurrula fusca (BL.) G
It was found that complexation of 1 with K+ ion in a molar ratio of 20:1 is essential for expression of the anti-tumor activity.2c perseitol is known as a naturally occurring heptitol, first isolated from avocado,[3] and several preparative methods for perseitol have been developed,[4] no stereocontrolled synthesis capable of producing 1 in complete enantio- and diastereo-controlled manner has yet been reported
Since we have developed an efficient preparation from furfural of the highly functionalized bicyclic enone 2 having the 7,8-dioxabicyclo[3.2.1]octane framework, in both enantiomeric forms, by employing either chemical[5] or enzymatic procedures,[6] and since we have demonstrated its potential[7] as a versatile chiral building block,[8] especially for ISSN 1551-7012
Summary
The leaves of a parasitic plant Scurrula fusca (BL.) G. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel 15 g, elution with EtOAc–hexane, 1:4 v/v) to give the exo- epoxide 3 (240 mg, 75%) as a colorless solid. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel, 10 g, elution with EtOAc–hexane, 1:1 v/v) to give the alcohol 4 (113 mg, 60%) as a colorless oil.
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