Enzymatic Synthesis of Selectively Protected Glycals

Hanessian S., 1983, Total Synthesis of Natural Products: The ‘Chiron Approach’

10.1021/cr00049a003

10.1016/0040-4020(84)85002-4

Roth W., 1963, Methods Carbohydr. Chem., 2, 405

10.1016/S0065-2318(08)60280-2

10.1016/S0065-2318(08)60204-8

10.1071/CH9760381

10.1016/S0040-4039(00)96025-8

10.1248/cpb.15.1367

10.1002/bit.260290515

10.1002/cjce.5450470410

10.1135/cccc19872347

10.1021/ja00280a068

10.1016/S0040-4039(00)96264-6

10.1021/ja00278a053

10.1016/S0040-4039(00)95884-2

10.1021/jo00248a046

The following lipases fromCandida cylindracea(LCC) were employed: L‐1754 Type VII from Sigma Chemie GmbH (“S‐VIP”) lipase AY‐20 from Amano Pharmaceutical Co.; lipase OF from Meito Sangyo Co. Ltd.; lipasePfromPseudomonas fluorescenswas supplied by Amano Pharmaceutical Co.

The lipases were used up to ten times; the decrease in enzymatic activity is dependent on the type of lipase and reaction. The retention of enzymatic activity is currently under investigation.

Greener T. W., 1981, Protective Groups in Organic Synthesis

For comparison: Treatment of1awith 1 equivalent of C6H5COCl/pyridine at 0°C gave8ain only 29% yield [3c].

Acyl‐group migrations were not observed in any of the reactions. All the given structures are consistent with the spectroscopic data.