Journal
TETRAHEDRON
Volume 67, Issue 51, Pages 9837-9843Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.09.079
Keywords
Total synthesis; Prins-pinacol rearrangement; 2-Oxonia[3,3]sigmatropic rearrangement; Mechanism; Cascade reaction; Natural products
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Funding
- NIH [NS-12389, GM-098601, NIH P30CA 33572]
- Lilly
- Allergan
- NSF
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This paper reports the first unambiguous evidence that the cascade synthesis of tetrahydrofuran-containing oxacyclic molecules depicted in Scheme 12 can take place by a 2-oxonia[3,3]sigmatropic/aldol mechanism rather than by a Prins cyclization/pinacol rearrangement sequence. The 8-oxabicyclo [3.2.1]octyl aldehyde products of this reaction, 20 and 29, were employed to complete the first total synthesis of the structurally remarkable isoindolone alkaloid (+)-aspergillin PZ (1). The lack of activity seen in two tumor cell lines for synthetic (+)-aspergillin PZ calls into question the suggestion that aspergillin PZ, like many aspochalasin diterpenes, might exhibit useful antitumor properties. (C) 2011 Elsevier Ltd. All rights reserved.
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