Toward the total synthesis of patellazole B: synthesis of an advanced C1-C25 fragment corresponding to the macrocyclic skeleton.
Publication Date
2018-09-26Journal Title
Org Biomol Chem
ISSN
1477-0520
Publisher
Royal Society of Chemistry (RSC)
Volume
16
Issue
37
Pages
8286-8291
Language
eng
Type
Article
Physical Medium
Print
Metadata
Show full item recordCitation
Phillips, A. W., Anketell, M., Balan, T., Lam, N., Williams, S., & Paterson, I. (2018). Toward the total synthesis of patellazole B: synthesis of an advanced C1-C25 fragment corresponding to the macrocyclic skeleton.. Org Biomol Chem, 16 (37), 8286-8291. https://doi.org/10.1039/c8ob01621f
Abstract
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.
Identifiers
External DOI: https://doi.org/10.1039/c8ob01621f
This record's URL: https://www.repository.cam.ac.uk/handle/1810/285150
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