Total synthesis of 8-deshydroxyajudazol B

Stephen Birkett; Danny Ganame; Bill C Hawkins; Sébastien Meiries; Tim Quach; Mark A Rizzacasa

doi:10.1021/ol200331u

Total synthesis of 8-deshydroxyajudazol B

Stephen Birkett, Danny Ganame, Bill C Hawkins, Sébastien Meiries, Tim Quach, Mark A Rizzacasa

Research output: Contribution to journal › Letter › Research › peer-review

29 Citations (Scopus)

Abstract

The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels-Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira coupling to form the C18-C19 bond. Partial alkyne reduction then afforded the target 4.

Original language	English
Pages (from-to)	1964-1967
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	8
DOIs	https://doi.org/10.1021/ol200331u
Publication status	Published - 15 Apr 2011
Externally published	Yes

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10.1021/ol200331u

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title = "Total synthesis of 8-deshydroxyajudazol B",

abstract = "The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels-Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira coupling to form the C18-C19 bond. Partial alkyne reduction then afforded the target 4.",

author = "Stephen Birkett and Danny Ganame and Hawkins, \{Bill C\} and S{\'e}bastien Meiries and Tim Quach and Rizzacasa, \{Mark A\}",

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doi = "10.1021/ol200331u",

language = "English",

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T1 - Total synthesis of 8-deshydroxyajudazol B

AU - Birkett, Stephen

AU - Ganame, Danny

AU - Hawkins, Bill C

AU - Meiries, Sébastien

AU - Quach, Tim

AU - Rizzacasa, Mark A

PY - 2011/4/15

Y1 - 2011/4/15

N2 - The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels-Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira coupling to form the C18-C19 bond. Partial alkyne reduction then afforded the target 4.

AB - The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels-Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira coupling to form the C18-C19 bond. Partial alkyne reduction then afforded the target 4.

UR - https://www.scopus.com/pages/publications/79955369535

U2 - 10.1021/ol200331u

DO - 10.1021/ol200331u

M3 - Letter

C2 - 21410165

AN - SCOPUS:79955369535

SN - 1523-7060

VL - 13

SP - 1964

EP - 1967

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Total synthesis of 8-deshydroxyajudazol B

Abstract

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