Total synthesis of the marine alkaloid halitulin

Markus R. Heinrich; Wolfgang Steglich; Martin G. Banwell; Yoel Kashman

doi:10.1016/j.tet.2003.02.005

Total synthesis of the marine alkaloid halitulin

Markus R. Heinrich, Wolfgang Steglich^*, Martin G. Banwell, Yoel Kashman

^*Corresponding author for this work

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

48 Citations (Scopus)

Abstract

The structure of the strongly cytotoxic marine alkaloid halitulin (1) has been confirmed by total synthesis and its absolute configuration determined as (15S). The synthesis follows a strategy previously reported by one of us and uses an efficient preparation of the quinoline-7,8-diol unit by modified Baeyer-Villiger and Skraup reactions. The O-benzyl protecting groups were removed in the last step of the synthesis by transfer hydrogenolysis without concomitant reduction of the quinoline ring. The method can be applied for the synthesis of halitulin analogues.

Original language	English
Pages (from-to)	9239-9247
Number of pages	9
Journal	Tetrahedron
Volume	59
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2003.02.005
Publication status	Published - 10 Nov 2003

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@article{93cbf75caf244b4bbebe86fd759d2925,

title = "Total synthesis of the marine alkaloid halitulin",

abstract = "The structure of the strongly cytotoxic marine alkaloid halitulin (1) has been confirmed by total synthesis and its absolute configuration determined as (15S). The synthesis follows a strategy previously reported by one of us and uses an efficient preparation of the quinoline-7,8-diol unit by modified Baeyer-Villiger and Skraup reactions. The O-benzyl protecting groups were removed in the last step of the synthesis by transfer hydrogenolysis without concomitant reduction of the quinoline ring. The method can be applied for the synthesis of halitulin analogues.",

keywords = "Baeyer-Villiger oxidation, Halitulin, Marine metabolites, Natural product synthesis, Quinoline-7,8-diols, Suzuki reaction",

author = "Heinrich, {Markus R.} and Wolfgang Steglich and Banwell, {Martin G.} and Yoel Kashman",

year = "2003",

month = nov,

day = "10",

doi = "10.1016/j.tet.2003.02.005",

language = "English",

volume = "59",

pages = "9239--9247",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "46",

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TY - JOUR

T1 - Total synthesis of the marine alkaloid halitulin

AU - Heinrich, Markus R.

AU - Steglich, Wolfgang

AU - Banwell, Martin G.

AU - Kashman, Yoel

PY - 2003/11/10

Y1 - 2003/11/10

N2 - The structure of the strongly cytotoxic marine alkaloid halitulin (1) has been confirmed by total synthesis and its absolute configuration determined as (15S). The synthesis follows a strategy previously reported by one of us and uses an efficient preparation of the quinoline-7,8-diol unit by modified Baeyer-Villiger and Skraup reactions. The O-benzyl protecting groups were removed in the last step of the synthesis by transfer hydrogenolysis without concomitant reduction of the quinoline ring. The method can be applied for the synthesis of halitulin analogues.

AB - The structure of the strongly cytotoxic marine alkaloid halitulin (1) has been confirmed by total synthesis and its absolute configuration determined as (15S). The synthesis follows a strategy previously reported by one of us and uses an efficient preparation of the quinoline-7,8-diol unit by modified Baeyer-Villiger and Skraup reactions. The O-benzyl protecting groups were removed in the last step of the synthesis by transfer hydrogenolysis without concomitant reduction of the quinoline ring. The method can be applied for the synthesis of halitulin analogues.

KW - Baeyer-Villiger oxidation

KW - Halitulin

KW - Marine metabolites

KW - Natural product synthesis

KW - Quinoline-7,8-diols

KW - Suzuki reaction

UR - http://www.scopus.com/inward/record.url?scp=0142196121&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2003.02.005

DO - 10.1016/j.tet.2003.02.005

M3 - Article

SN - 0040-4020

VL - 59

SP - 9239

EP - 9247

JO - Tetrahedron

JF - Tetrahedron

IS - 46

ER -

Total synthesis of the marine alkaloid halitulin

Abstract

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