𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of Topsentin-A, A Bisindole Alkaloid of the Marine Sponge Topsentia genitrix

✍ Scribed by J. C. Braekman; D. Daloze; C. Stoller

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
153 KB
Volume
96
Category
Article
ISSN
0037-9646

No coin nor oath required. For personal study only.

✦ Synopsis

ring sponge TOp8mtM g e n i t r k , has been achieved starting from 3-acetylindole.

The synthesis of topsentin-A, a bisindole alkaloid isolated from the ma-Recently, we reported the isolation from the marine sponge T o p e e n t i a g e n i t r k of three related basic compounds, topsentin-AU), -el(?) and -B2(2) pertaining to a new type of bisindole alkaloids. The structure determinations were based on their spectral properties and, in particular, on homo-and heterocorrelated 2D NWR experiments").

These derivatives are presumed to derive from the biocondensation of two tryptophan units. total synthesis of topsentin-A starting from 3-acetylindole.

This synthesis is based on the rearrangement, reported by Koga et al.( 283), of 1,1-dimethyl-1-phenacylhydrazinium bromide (1) into 12-phenyl-lH-imidazol-4yllphenylmethanone (2). of a N to N migration of the phenacyl to give l,l-dimethyl-2-phenacylhydrazine

📜 SIMILAR VOLUMES

One-Pot Synthesis of Diazine-Bridged Bis
One-Pot Synthesis of Diazine-Bridged Bisindoles and Concise Synthesis of the Marine Alkaloid Hyrtinadine A
✍ Boris O. A. Tasch; Eugen Merkul; Thomas J. J. Müller 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 166 KB

## Abstract Diazine‐bridged bisindoles are readily obtained from __N__‐Boc‐protected 3‐iodoindoles and 3‐iodo‐7‐azaindole in a pseudo three‐component reaction involving a one‐pot Masuda borylation–Suzuki arylation sequence. Some of the title compounds display promising cytotoxic properties. The ver