Abstract
A streamlined entry into the sesquiterpene lactone (SQL) cores of linearifolin and zaluzanin A is described. Stereochemistry is controlled through transformations uncovered by ISES (In Situ Enzymatic Screening). Absolute stereochemistry derives from kinetic resolution of 5-benzyloxypentene-1,2-oxide, utilizing a β-pinene-derived-Co(III)-salen. Relative stereochemistry (1,3-cis-fusion) is set via formal halometalation/carbocyclization, mediated by [Rh(O 2CC 3F 7) 2] 2/LiBr. Subsequent ring-closing metathesis (RCM-Grubbs II) yields the title exomethylene-δ-lactone SQL cores. In complementary fashion, RCM with Grubbs-I catalyst provides the oxabicyclo[3.3.1]nonyl core of xerophilusin R and zinagrandinolide.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 968-971 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 14 |
| Issue number | 4 |
| DOIs | |
| State | Published - Feb 17 2012 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Ginotra, S. K., Friest, J. A., & Berkowitz, D. B. (2012). Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: Exploiting combinatorial catalysis. Organic Letters, 14(4), 968-971. https://doi.org/10.1021/ol203088g