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image of A Novel Enantioselective Synthesis of Cryptophycins Unit A from Rocher’s Ester

Abstract

A novel synthesis of cryptophycin unit A in its enantiomerically pure form was achieved. In five steps, an enantiomeric mixture of unit A was initially prepared from trans-cinnamaldehyde. Subsequently, in its enantiomerically pure forms, unit A was prepared from Rocher’s ester in six steps, involving an essential aldehyde (2R,3E)-2-methyl-4-phenylbut-3-enal. The final step of this process involved two different approaches: a Reformatsky reaction of an essential aldehyde with tertbutyl 4-bromocrotonate and the vinylogous Mukaiyama aldol reaction with -Silyl ketene acetal in the presence of isopropyl alcohol and -tryptophane-based -phenyloxazaborolidinone, thereby resulting in the desired products in good overall yields and high enantioselectivities.

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2025-01-13
2025-04-07

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A Novel Enantioselective Synthesis of Cryptophycins Unit A from Rocher’s Ester
Bentham Science Publishers ; https://doi.org/10.2174/0115701786356555241215053133
/content/journals/loc/10.2174/0115701786356555241215053133
/content/journals/loc/10.2174/0115701786356555241215053133
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  • Article Type:     Research Article
Keywords: depsipeptide ; cytotoxicity ; vinylogous Mukaiyama aldol reaction ; Reformatsky reaction ; Cryptophycins ; antitumor agents

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