Toward the total synthesis of patellazole B: synthesis of an advanced C1–C25 fragment corresponding to the macrocyclic skeleton

文献信息

发布日期 2018-09-07

DOI 10.1039/C8OB01621F

影响因子 3.876

作者

Andrew W. Phillips, Matthew J. Anketell, Tudor Balan, Nelson Y. S. Lam, Simon Williams, Ian Paterson

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摘要

The patellazoles are a family of complex marine macrolides that exhibit potent cytotoxicity against cancer cell lines. However, despite extensive characterisation efforts, their full stereochemical assignment has remained elusive. We report our approach towards the synthesis-enabled structural elucidation of patellazole B (4), a 24-membered macrolide with 16 stereocentres and a signature thiazole-containing side chain. Our plan hinges upon isolating the unknown stereocentres into a single C20–C25 fragment to facilitate the flexible assembly of various possible diastereomers of an advanced C1–C25 fragment. Towards this end, a highly convergent and modular synthesis of one candidate diastereomer 37, corresponding to the patellazole B macrocyclic skeleton, has been achieved based on the strategic application of stereocontrolled aldol methodology, combined with Suzuki and Heck cross-coupling reactions.

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来源期刊

Organic & Biomolecular Chemistry

CiteScore: 3.4

自引率: 10.3%

年发文量: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Toward the total synthesis of patellazole B: synthesis of an advanced C1–C25 fragment corresponding to the macrocyclic skeleton

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来源期刊

Organic & Biomolecular Chemistry

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