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Literature DB >> 21877709

A concise total synthesis of (-)-maoecrystal Z.

Jacob Y Cha¹, John T S Yeoman, Sarah E Reisman.

Abstract

The first total synthesis of (-)-maoecrystal Z is described. The key steps of the synthesis include a diastereoselective Ti(III)-mediated reductive epoxide coupling reaction and a diastereoselective Sm(II)-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (-)-maoecrystal Z in only 12 steps from (-)-γ-cyclogeraniol.

Entities: Chemical

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Year: 2011 PMID： 21877709 DOI： 10.1021/ja2073356

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

21 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

10. Synthetic studies toward longeracemine: a SmI₂-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework.

Authors: Keita Komine; Kyle M Lambert; Quentin R Savage; Joshua B Cox; John L Wood
Journal: Chem Sci Date: 2020-07-30 Impact factor: 9.825

A concise total synthesis of (-)-maoecrystal Z.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Forging C(sp³)-C(sp³) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

3. Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid.

4. Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

5. Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal V.

6. Total synthesis of (±)-maoecrystal V.

Review 7. Total synthesis of complex terpenoids employing radical cascade processes.

8. Radicals in natural product synthesis.

9. Synthesis of Complex Diterpenes: Strategies Guided by Oxidation Pattern Analysis.

10. Synthetic studies toward longeracemine: a SmI₂-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework.