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Asymmetric Syntheses of Pectenotoxins-4 and -8, Part I: Synthesis of the C1–C19 Subunit

✍ Scribed by David A. Evans; Hemaka A. Rajapakse; Dirk Stenkamp

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
124 KB
Volume
41
Category
Article
ISSN
0044-8249

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✦ Synopsis

The first members of the pectenotoxin family of marine natural products were isolated off the northeastern coast of Japan in 1985. Subsequently, ten members of this group have been identified. The structural diversity within the pectenotoxins stems from variations in the oxidation state at C43, as well as the differing configurations of the AB spiroketal portion of the structures. Pectenotoxin-2 (C43 ¼ Me) is cytotoxic towards human lung, colon, and breast cancer cell lines with LC 50 values in the nanomolar range. [1c] Pectenotox-COMMUNICATIONS

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Asymmetric Syntheses of Pectenotoxins-4
Asymmetric Syntheses of Pectenotoxins-4 and -8, Part II: Synthesis of the C20–C30 and C31–C40 Subunits and Fragment Assembly
✍ David A. Evans; Hemaka A. Rajapakse; Anna Chiu; Dirk Stenkamp 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 107 KB 👁 1 views

In the preceding communication, [1] the proposed synthesis plan identified the two principal pectenotoxin-4 subunits II and III (Figure 1). It was our intention to couple these fragments through the alkylation of the metalloenamine derived from hydrazone III, readily available from the coupling of a