Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes: Application to the synthesis of a C13C25 segment of bafilomycin A1

Ian Paterson; Shelley Bower; Malcolm D. McLeod

doi:10.1016/0040-4039(94)02205-P

Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes: Application to the synthesis of a C₁₃C₂₅ segment of bafilomycin A₁

Ian Paterson^*
, Shelley Bower
, Malcolm D. McLeod

^*Corresponding author for this work

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

45 Citations (Scopus)

Abstract

A boron-mediated, syn-aldol coupling between ethyl ketone 8 and aldehyde 9, followed by directed hydrogenation at C₁₆ and acetonide hydrolysis, gives the C₁₃C₂₅ segment 6 of bafilomycin A₁.

Original language	English
Pages (from-to)	175-178
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	1
DOIs	https://doi.org/10.1016/0040-4039(94)02205-P
Publication status	Published - 2 Jan 1995
Externally published	Yes

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@article{5b00ea9688fa4a1d8c5755fb1c89c3fb,

title = "Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes: Application to the synthesis of a C13C25 segment of bafilomycin A1",

abstract = "A boron-mediated, syn-aldol coupling between ethyl ketone 8 and aldehyde 9, followed by directed hydrogenation at C16 and acetonide hydrolysis, gives the C13C25 segment 6 of bafilomycin A1.",

author = "Ian Paterson and Shelley Bower and McLeod, \{Malcolm D.\}",

year = "1995",

month = jan,

day = "2",

doi = "10.1016/0040-4039(94)02205-P",

language = "English",

volume = "36",

pages = "175--178",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Ltd.",

number = "1",

}

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T1 - Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes

T2 - Application to the synthesis of a C13C25 segment of bafilomycin A1

AU - Paterson, Ian

AU - Bower, Shelley

AU - McLeod, Malcolm D.

PY - 1995/1/2

Y1 - 1995/1/2

N2 - A boron-mediated, syn-aldol coupling between ethyl ketone 8 and aldehyde 9, followed by directed hydrogenation at C16 and acetonide hydrolysis, gives the C13C25 segment 6 of bafilomycin A1.

AB - A boron-mediated, syn-aldol coupling between ethyl ketone 8 and aldehyde 9, followed by directed hydrogenation at C16 and acetonide hydrolysis, gives the C13C25 segment 6 of bafilomycin A1.

UR - https://www.scopus.com/pages/publications/0028891048

U2 - 10.1016/0040-4039(94)02205-P

DO - 10.1016/0040-4039(94)02205-P

M3 - Article

AN - SCOPUS:0028891048

SN - 0040-4039

VL - 36

SP - 175

EP - 178

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes: Application to the synthesis of a C₁₃C₂₅ segment of bafilomycin A₁

Abstract

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