The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment
Author(s)
Paterson, I
Coster, MJ
Chen, DYK
Oballa, RM
Wallace, DJ
Norcross, RD
Griffith University Author(s)
Year published
2005
Metadata
Show full item recordAbstract
The convergent synthesis of the C1-C15 AB-spiroacetal subunit 2 of altohyrtin A/spongistatin 1 (1) is described. This highly stereocontrolled synthesis relies on matched boron aldol reactions of chiral methyl ketones, under Ipc2BCl mediation, to establish the C5, C9 and C11 stereocentres, and formation of the desired thermodynamic spiroacetal under acidic conditions. The scalable synthetic sequence developed provided access to multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4.The convergent synthesis of the C1-C15 AB-spiroacetal subunit 2 of altohyrtin A/spongistatin 1 (1) is described. This highly stereocontrolled synthesis relies on matched boron aldol reactions of chiral methyl ketones, under Ipc2BCl mediation, to establish the C5, C9 and C11 stereocentres, and formation of the desired thermodynamic spiroacetal under acidic conditions. The scalable synthetic sequence developed provided access to multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4.
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Journal Title
Organic & Biomolecular Chemistry
Volume
3
Subject
Medicinal and biomolecular chemistry
Organic chemistry