Jump to main content
Jump to site search

Issue 1, 2003
Previous Article Next Article

A formal total synthesis of (+)-apicularen A: base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products

Author affiliations

Abstract

A synthesis of apicularen precursor (−)-6 in 18 steps from D-glucal is reported. As (+)-6 has been converted into the potent, naturally occurring salicylate anti-cancer agent, (−)-apicularen A in 8 steps, this study constitutes a formal total synthesis of (+)-apicularen A. Key steps in the synthetic route include: (i) useful D-glucal elaboration processes, (ii) organometallic displacements at carbohydrate C-6 triflates using Knochel-type and related functionalised, aromatic Grignard reagents, (iii) stereoselective allyltrimethylsilane–acetal reactions generating C-allyl systems, (iv) stereocontrolled aldehyde allylation processes from both substrate and reagent, and (v) a novel Keck-type macrolactonisation. In addition, preliminary studies are reported in which a procedure has been devised to convert apicularen-derived intermediates into salicylihalamide-like products.

Graphical abstract: A formal total synthesis of (+)-apicularen A: base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products

Back to tab navigation

Publication details

The article was received on 01 Oct 2002, accepted on 21 Oct 2002 and first published on 05 Dec 2002


Article type: Paper
DOI: 10.1039/B209637B
Org. Biomol. Chem., 2003,1, 104-116

  •   Request permissions

    A formal total synthesis of (+)-apicularen A: base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products

    A. Lewis, I. Stefanuti, S. A. Swain, S. A. Smith and R. J. K. Taylor, Org. Biomol. Chem., 2003, 1, 104
    DOI: 10.1039/B209637B

Search articles by author

Spotlight

Advertisements