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Total synthesis of the antitumor agent (−)-laulimalide

✍ Scribed by Johann Mulzer; Martin Hanbauer

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
122 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A stereocontrolled synthesis of the title compound is described. Key steps are an allylsilane addition to a chiral acetal as the major coupling step and a Yamaguchi macrolactonization for ring closure.

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A chirally catalysed ene reaction in a n
A chirally catalysed ene reaction in a novel formal total synthesis of the antitumor agent laulimalide
✍ Michael R Pitts; Johann Mulzer 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 182 KB

A short highly efficient synthesis of the C3 C16 fragment 2 of laulimalide 1 is described. Fragment 2 was a key intermediate in a previous approach and thus constitutes a formal total synthesis with improved efficiency. The key steps are an Evans' alkylation, a Brown allylation and a chirally cataly

Synthesis of the C15–C27 fragment of the
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✍ E.Kate Dorling; Elisabeth Öhler; Johann Mulzer 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 129 KB

A stereocontrolled synthesis of the C15±C27 fragment of laulimalide is described. Key features are a divergent±convergent synthesis from (R)-glycidol, an interesting formation of a trisubstituted double bond via ring closing metathesis with Grubbs' ruthenium catalyst and a site selective protection