Towards a Synthesis of Naphthalene Derived Natural Products 英文参考文献.docVIP

Molecules 2005, 10, 1272–1278 molecules ISSN 1420-3049 Towards a Synthesis of Naphthalene Derived Natural Products Malcolm W. B. McCulloch and Russell A. Barrow* Microbial Natural Product Research Group, Department of Chemistry, Australian National University, Canberra ACT 0200, Australia; Tel. +(61)261253419, Fax +(61)261250760. *Author to whom correspondence should be addressed; e-mail: rab@.au Received: 3 December 2004 / Accepted: 28 April 2005 / Published: 31 October 2005 Abstract: Dieckmann-type cyclization reactions have been employed in the synthesis of the alkyl substituted naphthoquinone 11 and the naphthalenes 10 and 12. Various conditions for the benzylic oxidation of these compounds have been investigated with a view towards the synthesis of some naphthalene based natural products. Keywords: Naphthalenes, benzylic oxidation, naphtho-γ-pyrone. Introduction A large number of naphthalene derived natural products are based on a substituted naphthalene skeleton as represented by 1. These include: the naphthyl ketone derivative guieranone A (2) [1], heterocyclic derivatives like the linear naphtho-γ-pyrone (NGP) rubrofusarin (3) [2-3], and naphthoquinones such as the crinoid derived pigment 4 [4]. Given that 3 is the only linear NGP based natural product to have been synthesized, [5-7] and that many structurally related NGPs possessing biological properties have been isolated, we are interested in developing a general synthesis of NGPs and as a corollary this synthesis should be extendable to related naphthalene derived natural products represented here by 2 and 4. OMe OH O OMe OMe O OH OH O O OH O O Pr MeO OH MeO OMe MeO NaO3SO OH O 1 2 3 4  Molecules 2005, 10, X 1273 Synthetic methods to access these substituted naphthalene based compounds are limited. While the 2-acetyl naphthalene 1 could serve as a starting material in the synthesis of the target compounds, the synt