The preparation of 9-substituted Δ5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C

Grant A. McNaughton-Smith; Richard J.K. Taylor

doi:10.1016/0040-4020(95)01028-9

The preparation of 9-substituted Δ⁵-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C

Grant A. McNaughton-Smith, Richard J.K. Taylor

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

Abstract

Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladium-catalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.

Original language	English
Pages (from-to)	2113-2124
Number of pages	12
Journal	Tetrahedron
Volume	52
Issue number	6
DOIs	https://doi.org/10.1016/0040-4020(95)01028-9
Publication status	Published - 5 Feb 1996

Access to Document

10.1016/0040-4020(95)01028-9

Cite this

@article{430de8781df3418ea002b1e6533a7bc9,

title = "The preparation of 9-substituted Δ5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C",

abstract = "Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladium-catalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.",

author = "McNaughton-Smith, {Grant A.} and Taylor, {Richard J.K.}",

year = "1996",

month = feb,

day = "5",

doi = "10.1016/0040-4020(95)01028-9",

language = "English",

volume = "52",

pages = "2113--2124",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "6",

}

TY - JOUR

T1 - The preparation of 9-substituted Δ5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C

AU - McNaughton-Smith, Grant A.

AU - Taylor, Richard J.K.

PY - 1996/2/5

Y1 - 1996/2/5

N2 - Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladium-catalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.

AB - Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladium-catalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.

UR - http://www.scopus.com/inward/record.url?scp=0030034367&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(95)01028-9

DO - 10.1016/0040-4020(95)01028-9

M3 - Article

AN - SCOPUS:0030034367

SN - 0040-4020

VL - 52

SP - 2113

EP - 2124

JO - Tetrahedron

JF - Tetrahedron

IS - 6

ER -

The preparation of 9-substituted Δ5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C

Abstract

Access to Document

Other files and links

Cite this

The preparation of 9-substituted Δ⁵-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C