Unusual Dimerization of 3-Methylphenalen-1-One, Leading to a Chiral Heptacyclic Oxocin

S. Pogodin; M. Thirumalaikumar; S. Cohen; I. Agranat

doi:10.2174/157017805774296867

ISSN: 1570-1786
E-ISSN: 1875-6255

Unusual Dimerization of 3-Methylphenalen-1-One, Leading to a Chiral Heptacyclic Oxocin
Authors: S. Pogodin¹, M. Thirumalaikumar², S. Cohen³ and I. Agranat⁴
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¹ Department of Organic Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel. ² Department of Organic Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel. ³ Department of Organic Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel. ⁴ Department of Organic Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel.
Source: Letters in Organic Chemistry, Volume 2, Issue 7, Nov 2005, p. 640 - 643
DOI: https://doi.org/10.2174/157017805774296867
- Available online: 01 Nov 2005

Abstract

A diastereoselective reaction of 3-methyl-1H-phenalen-1-one (6) with Lawesson's reagent afforded 8a,15a-dihydro-7,8a,16-trimethyl-7,16-epoxy-7H,15H,16H-naphtho[1,8-ef]phenaleno[1,2-b]oxocin-15-one (10), in 82% yield. The formation mechanism of 10 involves a Michael addition of a naphthopyrane intermediate to 6, followed by an intramolecular aldol condensation. The structure of a single enantiomer of 10 (7R, 8aR, 15aR, 16S or 7S, 8aS, 15aS, 16R) was elucidated by X-ray crystallography.

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2005-11-01

2025-10-29

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Article Type: Review Article

Keyword(s): chirality; diastereoselective reaction; lawessons reagent; novel aromatic chemistry; phenalenes; x-ray crystallography

Unusual Dimerization of 3-Methylphenalen-1-One, Leading to a Chiral Heptacyclic Oxocin

Abstract

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