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

  


Authors: Trauner, D.; Danishefsky, S. J.
Article 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.
Keywords: nonhuman; natural product; reaction analysis; chemical reaction; synthesis; stereochemistry; spiro compound; lactam derivative; alkaloid; sponge (porifera); marine environment; article; chlorine derivative; quinolizidine derivative; mannich base
Journal Title: Tetrahedron Letters
Volume: 40
Issue: 36
ISSN: 0040-4039
Publisher: Pergamon-Elsevier Science Ltd  
Date Published: 1999-09-03
Start Page: 6513
End Page: 6516
Language: English
DOI: 10.1016/s0040-4039(99)01170-3
PROVIDER: scopus
DOI/URL:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033520211&partnerID=40&md5=9e27141accdd8bcda83547e2191b0479
Notes: Article -- Export Date: 16 August 2016 -- Source: Scopus
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MSK Authors
  1. Dirk Trauner
    4 Trauner
  2. Samuel J Danishefsky
    539 Danishefsky
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