THE TOTAL SYNTHESIS OF SCYTOPHYCIN-C - PART 2 - SYNTHESIS OF SCYTOPHYCIN-C FROM THE PROTECTED SECO ACID

Authors
PATERSON I WATSON C YEUNG KS WARD RA WALLACE PA
Citation
I. Paterson et al., THE TOTAL SYNTHESIS OF SCYTOPHYCIN-C - PART 2 - SYNTHESIS OF SCYTOPHYCIN-C FROM THE PROTECTED SECO ACID, Tetrahedron, 54(39), 1998, pp. 11955-11970
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
39
Year of publication
1998
Pages
11955 - 11970
Database
ISI
SICI code
0040-4020(1998)54:39<11955:TTSOS->2.0.ZU;2-O
Abstract
Scytophycin C (1) was synthesised in 8 steps from the fully protected seco acid 2. Key steps include: (i) a high yielding macrolactonisation reaction of 15 followed by regioselective isomerisation of the undesi red, 24-membered macrolide, 18 --> 16; (ii) the chemoselective oxidati on steps, 16 --> 6 and 7 --> 8; (iii) the P2O5-promoted condensation o f 8 with HN(Me)CHO to install the N-methyl vinylformamide moiety in 1. (C) 1998 Elsevier Science Ltd. All rights reserved.