Racemic and enantiopure targets containing the 6,8-dioxabicycio [3.2.1]octane skeleton, can be conveniently synthesized from monocyclic diene precursors using an intramolecular ruthenium-catalyzed ring-closing metathesis reaction as the key step.
Total Synthesis of (+)-Cryptocaryalactone and of a Diastereoisomer of (+)-Strictifolione via Ring-Closing Metathesis (RCM) and Olefin Cross-Metathesis (CM)
✍ Scribed by Gowravaram Sabitha; Bhaskar Vangala; S. Siva Sankara Reddy; Jhillu S. Yadav
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- German
- Weight
- 217 KB
- Volume
- 93
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Ring‐closing metathesis (RCM) and olefin cross‐metathesis (CM) reactions were used as the key steps for the synthesis of (+)‐cryptocaryalactone (1) and the first synthesis of the diastereoisomer 3 of (+)‐strictifolione, starting from the commercially available L‐malic acid (=(2__S__)‐2‐hydroxybutanedioic acid).
📜 SIMILAR VOLUMES
## A&Wrack Lactones and lactams 4-6 were synthesized from a series of acyclic dienes 1-3 via ringclosing olefin metathesis, as shown in equation 1. The geometry of the resulting double bond was determined, and the UZratios compared to values from molecular mechanics calculations.