Revision of the structure of haliclorensin to (S)-7-methyl-1,5-diazacyclotetradecane and confirmation of the new structure by synthesis

Markus R. Heinrich; Yoel Kashman; Peter Spiteller; Wolfgang Steglich

doi:10.1016/S0040-4020(01)01020-1

Revision of the structure of haliclorensin to (S)-7-methyl-1,5-diazacyclotetradecane and confirmation of the new structure by synthesis

Markus R. Heinrich, Yoel Kashman, Peter Spiteller, Wolfgang Steglich

School of Chemistry

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

Abstract

A reinvestigation of the marine alkaloid haliclorensin led to a revision of the proposed structure to 7-methyl-1,5-diazacyclotetradecane. The new structure was confirmed by total synthesis of both optical forms. According to chiroptical measurements and GC-MS investigations, natural haliclorensin consists of a 3:1 mixture of the (S)- and (R)-enantiomers.

Original language	English
Pages (from-to)	9973-9978
Number of pages	6
Journal	Tetrahedron
Volume	57
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4020(01)01020-1
State	Published - 10 Dec 2001

Keywords

Alkaloids
Haliclorensin
Marine metabolites
Metathesis
Stereochemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/S0040-4020(01)01020-1

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abstract = "A reinvestigation of the marine alkaloid haliclorensin led to a revision of the proposed structure to 7-methyl-1,5-diazacyclotetradecane. The new structure was confirmed by total synthesis of both optical forms. According to chiroptical measurements and GC-MS investigations, natural haliclorensin consists of a 3:1 mixture of the (S)- and (R)-enantiomers.",

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AU - Heinrich, Markus R.

AU - Kashman, Yoel

AU - Spiteller, Peter

AU - Steglich, Wolfgang

PY - 2001/12/10

Y1 - 2001/12/10

N2 - A reinvestigation of the marine alkaloid haliclorensin led to a revision of the proposed structure to 7-methyl-1,5-diazacyclotetradecane. The new structure was confirmed by total synthesis of both optical forms. According to chiroptical measurements and GC-MS investigations, natural haliclorensin consists of a 3:1 mixture of the (S)- and (R)-enantiomers.

AB - A reinvestigation of the marine alkaloid haliclorensin led to a revision of the proposed structure to 7-methyl-1,5-diazacyclotetradecane. The new structure was confirmed by total synthesis of both optical forms. According to chiroptical measurements and GC-MS investigations, natural haliclorensin consists of a 3:1 mixture of the (S)- and (R)-enantiomers.

KW - Alkaloids

KW - Haliclorensin

KW - Marine metabolites

KW - Metathesis

KW - Stereochemistry

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VL - 57

SP - 9973

EP - 9978

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 50

ER -

Revision of the structure of haliclorensin to (S)-7-methyl-1,5-diazacyclotetradecane and confirmation of the new structure by synthesis

Abstract

Keywords

UN SDGs

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