An approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B

John M. Gardiner; Philip E. Giles; María Luz Martín Martín

doi:10.1016/S0040-4039(02)01071-7

An approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B

John M. Gardiner, Philip E. Giles, María Luz Martín Martín

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

Abstract

A route towards synthesis of analogues of the pumilotoxin/allopumilotoxin side-chain is described. The C15,C16 diol was introduced by asymmetric dihydroxylation using AD-mix β of C10,C17 eneyneone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using thioaryl conjugate addition to yneones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	5415-5418
Number of pages	3
Journal	Tetrahedron Letters
Volume	43
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(02)01071-7
Publication status	Published - 29 Jul 2002

Keywords

Addition reaction (conjugate; prepn. of C12 oxo analogs of the side chain of pumiliotoxin B, allopumiliotoxin 339A and B); Asymmetric synthesis and induction; Grignard reaction (prepn. of C12 oxo analogs of the side chain of pumiliotoxin B, allopumiliotoxin 339A and B); Dihydroxylation (stereoselective; prepn. of C12 oxo analogs of the side chain of pumiliotoxin B, allopumiliotoxin 339A and B)

Access to Document

10.1016/S0040-4039(02)01071-7

Cite this

@article{1387f0a9e1994be190d27f95120200a6,

title = "An approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B",

abstract = "A route towards synthesis of analogues of the pumilotoxin/allopumilotoxin side-chain is described. The C15,C16 diol was introduced by asymmetric dihydroxylation using AD-mix β of C10,C17 eneyneone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using thioaryl conjugate addition to yneones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

keywords = "Addition reaction (conjugate; prepn. of C12 oxo analogs of the side chain of pumiliotoxin B, allopumiliotoxin 339A and B); Asymmetric synthesis and induction; Grignard reaction (prepn. of C12 oxo analogs of the side chain of pumiliotoxin B, allopumiliotoxin 339A and B); Dihydroxylation (stereoselective; prepn. of C12 oxo analogs of the side chain of pumiliotoxin B, allopumiliotoxin 339A and B)",

author = "Gardiner, {John M.} and Giles, {Philip E.} and {Mart{\'i}n Mart{\'i}n}, {Mar{\'i}a Luz}",

year = "2002",

month = jul,

day = "29",

doi = "10.1016/S0040-4039(02)01071-7",

language = "English",

volume = "43",

pages = "5415--5418",

journal = "Tetrahedron Letters",

issn = "1873-3581",

publisher = "Elsevier BV",

number = "31",

}

TY - JOUR

T1 - An approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B

AU - Gardiner, John M.

AU - Giles, Philip E.

AU - Martín Martín, María Luz

PY - 2002/7/29

Y1 - 2002/7/29

N2 - A route towards synthesis of analogues of the pumilotoxin/allopumilotoxin side-chain is described. The C15,C16 diol was introduced by asymmetric dihydroxylation using AD-mix β of C10,C17 eneyneone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using thioaryl conjugate addition to yneones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues. © 2002 Elsevier Science Ltd. All rights reserved.

AB - A route towards synthesis of analogues of the pumilotoxin/allopumilotoxin side-chain is described. The C15,C16 diol was introduced by asymmetric dihydroxylation using AD-mix β of C10,C17 eneyneone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using thioaryl conjugate addition to yneones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues. © 2002 Elsevier Science Ltd. All rights reserved.

KW - Addition reaction (conjugate; prepn. of C12 oxo analogs of the side chain of pumiliotoxin B, allopumiliotoxin 339A and B); Asymmetric synthesis and induction; Grignard reaction (prepn. of C12 oxo analogs of the side chain of pumiliotoxin B, allopumiliotox

U2 - 10.1016/S0040-4039(02)01071-7

DO - 10.1016/S0040-4039(02)01071-7

M3 - Article

SN - 1873-3581

VL - 43

SP - 5415

EP - 5418

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

An approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B

Abstract

Keywords

Access to Document

Fingerprint

Cite this