The dolastatins 16. Synthesis of dolaphenine

George Pettit; Fiona Hogan; Douglas D. Burkett; Sheo B. Singh; Darko Kantoci; Jayaram Srirangam; Michael D. Williams

doi:10.3987/com-93-s(b)2

The dolastatins 16. Synthesis of dolaphenine

George Pettit, Fiona Hogan, Douglas D. Burkett, Sheo B. Singh, Darko Kantoci, Jayaram Srirangam, Michael D. Williams

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Abstract

Synthesis of dolaphenine (2), the thiazole-containing unit of the strongly antineoplastic peptide dolastatin 10 (1), has been summarized. While conversion (4→7 or 4→11) of phenylalanine to thiazolidines (7) or thiazolines (11) was routinely uneventful, a dependable procedure for dehydrogenation of these intermediates to dolaphenine (2, Doe) proved elusive. While several types of specially prepared manganese dioxide were found most effective for the dehydrogenation, yields of dolaphenine varied from almost nil to over 70%. Some of these reactions resulted in partial to complete racemization of the phenylalanine derived chiral carbon.

Original language	English (US)
Pages (from-to)	81-100
Number of pages	20
Journal	Heterocycles
Volume	39
Issue number	1
DOIs	https://doi.org/10.3987/com-93-s(b)2
State	Published - Dec 31 1994

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "Synthesis of dolaphenine (2), the thiazole-containing unit of the strongly antineoplastic peptide dolastatin 10 (1), has been summarized. While conversion (4→7 or 4→11) of phenylalanine to thiazolidines (7) or thiazolines (11) was routinely uneventful, a dependable procedure for dehydrogenation of these intermediates to dolaphenine (2, Doe) proved elusive. While several types of specially prepared manganese dioxide were found most effective for the dehydrogenation, yields of dolaphenine varied from almost nil to over 70%. Some of these reactions resulted in partial to complete racemization of the phenylalanine derived chiral carbon.",

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AU - Burkett, Douglas D.

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AU - Srirangam, Jayaram

AU - Williams, Michael D.

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AB - Synthesis of dolaphenine (2), the thiazole-containing unit of the strongly antineoplastic peptide dolastatin 10 (1), has been summarized. While conversion (4→7 or 4→11) of phenylalanine to thiazolidines (7) or thiazolines (11) was routinely uneventful, a dependable procedure for dehydrogenation of these intermediates to dolaphenine (2, Doe) proved elusive. While several types of specially prepared manganese dioxide were found most effective for the dehydrogenation, yields of dolaphenine varied from almost nil to over 70%. Some of these reactions resulted in partial to complete racemization of the phenylalanine derived chiral carbon.

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The dolastatins 16. Synthesis of dolaphenine

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