REARRANGEMENT OF A FURO[3,2-B]NAPHTHO[2,1-D]FURAN TO A PYRANONAPHTHOQUINONE

Brimble, Margaret; HODGES, R; STUART, SJ

REARRANGEMENT OF A FURO[3,2-B]NAPHTHO[2,1-D]FURAN TO A PYRANONAPHTHOQUINONE

Brimble, Margaret ; HODGES, R ; STUART, SJ

Identifier: http://hdl.handle.net/2292/8120

Issue Date: 1988-01-01

Reference: TETRAHEDRON LETT 29(46):5987-5990 1988

Rights: Copyright: 1988 Elsevier Ltd.

Rights (URI): https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm

Abstract:

The ceric ammonium nitrate oxidation of the furo(3,2-b]naphtho[2,l-d]furan-8(9H)- ones (5c,5d) gave the rearranged hemiketals (llc,lld) in 72-76% yield. -- Reduction of the hemiketals (llc,lld) provided an entry to a pyranonaphthoquinone with a fused Y-lactone as -- present in the pyranonaphthoquinone antibiotics kalafungin (5) and nanaomycin D (I).

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