Abstract
Pericosine E (6), a metabolite of Periconia byssoides OUPS-N133 was originally isolated from the sea hare Aplysia kurodai, which exists as an enantiomeric mixture in nature. The enantiospecific syntheses of both enantiomers of Periconia byssoides OUPS-N133 has been achieved, along with six stereoisomers, using a common simple synthetic strategy. For these efficient syntheses, highly regio- and steroselective processes for the preparation of bromohydrin and anti-epoxide intermediates were applied. In order to access the unique O-linked carbadisaccharide structure, coupling of chlorohydrin as a donor and anti-epoxide as an acceptor was achieved using catalytic BF3·Et2O. Most of the synthesized compounds exhibited selectively significant inhibitory activity against α-glycosidase derived from yeast. The strongest analog showed almost 50 times the activity of the positive control, deoxynojirimycin.
Highlights
As the first WHO Global report says “422 million adults were living with diabetes in 2014” and “diabetes caused 1.5 million death in 2012”, conquering diabetes or obesity is one of the most serious problems facing the humankind [1]
In the course of our continuing studies on the synthesis of bioactive marine natural products, we have studied and reported on the total syntheses of pericosines [9,10,11,12,13,14,15]
Donor 9 could be derived from syn-epoxide 11, which corresponds with a pericoxide proven to be donor 9 could be derived from syn‐epoxide 11, which corresponds with a pericoxide proven to be the precursor of pericosine A in the culture of Tolypocladium sp. [27]
Summary
As the first WHO Global report says “422 million adults were living with diabetes in 2014” and “diabetes caused 1.5 million death in 2012”, conquering diabetes or obesity is one of the most serious problems facing the humankind [1]. Shing and Hudlicky independently synthesized such molecules, providing a new class of unique glycosidase inhibitors [4,5,6,7] As this background shows, the synthetic study of carba-oligosaccharides as potential glycosidase inhibitors is a challenging step into a new research area for diabetes drugs discovery. Our synthetic strategy towards pericosines has changed to a biomimetic biomimetic method, in which two kinds of epoxides act as common intermediates [12,13,14,15]. Stereo‐controlled ringMK7607, opening using of allylic oxidesand stereo-controlled ringand opening of allylic by Lewis These reported studies implied thatand the co-workers syntheses of[28].
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