Jump to main content
Jump to site search


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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 09 Jul 2018, accepted on 05 Sep 2018 and first published on 07 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01621F
Citation: Org. Biomol. Chem., 2018, Advance Article
  •   Request permissions

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

    A. W. Phillips, M. J. Anketell, T. Balan, N. Y. S. Lam, S. Williams and I. Paterson, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01621F

Search articles by author

Spotlight

Advertisements