Studies towards the total synthesis of halichlorine: Asymmetric synthesis of the spiroquinolizidine subunit

Dirk Trauner; Samuel J. Danishefsky

doi:10.1016/S0040-4039(99)01170-3

Studies towards the total synthesis of halichlorine: Asymmetric synthesis of the spiroquinolizidine subunit

Dirk Trauner, Samuel J. Danishefsky

Chemistry

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

Abstract

The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure.

Original language	English (US)
Pages (from-to)	6513-6516
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4039(99)01170-3
State	Published - Sep 3 1999

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)01170-3

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title = "Studies towards the total synthesis of halichlorine: Asymmetric synthesis of the spiroquinolizidine subunit",

abstract = "The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure.",

author = "Dirk Trauner and Danishefsky, {Samuel J.}",

note = "Funding Information: This work was supported by the National Institutes of Health \[grant numbers: CA28824 (S.J.D.) and CA-08748 (S.K.I. core grant)\]. We thank the Schering Research Foundation, Berlin for financial support and Dr. George Sukenick for mass spectral analyses.",

year = "1999",

month = sep,

day = "3",

doi = "10.1016/S0040-4039(99)01170-3",

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journal = "Tetrahedron Letters",

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T1 - Studies towards the total synthesis of halichlorine

T2 - Asymmetric synthesis of the spiroquinolizidine subunit

AU - Trauner, Dirk

AU - Danishefsky, Samuel J.

N1 - Funding Information: This work was supported by the National Institutes of Health \[grant numbers: CA28824 (S.J.D.) and CA-08748 (S.K.I. core grant)\]. We thank the Schering Research Foundation, Berlin for financial support and Dr. George Sukenick for mass spectral analyses.

PY - 1999/9/3

Y1 - 1999/9/3

N2 - The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure.

AB - The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure.

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U2 - 10.1016/S0040-4039(99)01170-3

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M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Studies towards the total synthesis of halichlorine: Asymmetric synthesis of the spiroquinolizidine subunit

Abstract

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