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Stereoselective synthesis of the bicyclo[5.3.0]decane portion of the diterpene antibiotic guanacastepene using a pyrylium-ylide [5+2] cycloaddition reaction

✍ Scribed by Philip Magnus; Michael J Waring; Cyril Ollivier; Vince Lynch

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
127 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of 14 with Ac 2 O/Et 3 N resulted in [5+2] cyclization to give 2, which was further elaborated into 20, thus establishing the required stereochemistry in the top-half of guanacastepene 1.

📜 SIMILAR VOLUMES

Erratum to “Stereoselective synthesis of
Erratum to “Stereoselective synthesis of the bicyclo[5.3.0]decane portion of the diterpene antibiotic guanacastepene using a pyrylium-ylide [5+2] cycloaddition reaction”: [Tetrahedron Lett. 42 (2001) 4947–4950]
✍ Philip Magnus; Michael J. Waring; Cyril Ollivier; Vince Lynch 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 30 KB

Table 1. Reactions of 19 with various Me transfer reagents (product ratios of 20:21:22) 20 Conditions 21 22

Construction of the 5,10b-Phenanthridine
Construction of the 5,10b-Phenanthridine Skeleton Using [3+2]-Cycloaddition of a Non-Stabilized Azomethine Ylide: Total Synthesis of (±)-Maritidine and (±)-Crinine Alkaloids
✍ Ganesh Pandey; Nishant R. Gupta; Smita R. Gadre 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 902 KB

## Abstract Vicinal quaternary and tertiary stereocenters of the 5,10b‐phenanthridine skeleton **1** are constructed simultaneously in one step by the [3+2]‐cycloaddition of non‐stabilized azomethine ylide **9**, generated by sequential double desilylation of **10** utilizing silver(I) fluoride as