1448755-99-4Relevant articles and documents
Synthesis of macrosporin and related 9,10-anthraquinones by biomimetic polyketide aromatization and cyclization of 6-benzylresorcylates
Cordes, Jens,Barrett, Anthony G. M.
, p. 1318 - 1326 (2013/04/10)
This paper describes the synthesis of an array of 9,10-anthraquinones 2 by initial preparation of 6-benzylresorcylates 3 from oxo-dioxinone precursors 4 and their subsequent conversion to anthrones by cyclization and oxidation. Resorcylates 3 were obtained by an improved two-step procedure from oxo ester 5 and acyl chlorides 6. These methods were applied in a seven-step synthesis of the fungal natural product macrosporin (1). A new synthetic approach to 9,10-anthraquinones was developed. Selective Claisen condensation of an allyl γ-dioxinyl-β-oxo ester with arylacetyl chlorides, Pd-catalyzed deallylation, decarboxylation and aromatization gave 6-(arylmethyl)resorcylates. Subsequent acid-mediated cyclization and oxidation with CAN gave target anthraquinones, one of these being the fungal natural product macrosporin. Copyright