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

✍ Scribed by Dirk Trauner; Samuel J Danishefsky

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
208 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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