Studies in macrolide synthesis: Stereocontrolled synthesis of a C1C13 segment of concanamycin A
✍ Scribed by Ian Paterson; Malcolm D. McLeod
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 329 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The Ct-Ct3 segment 6 of concanamycin A (1) was prepared by a highly stereocontrolled route (87% overall ds) in 16 steps from the ester 9. Key steps are the one-pot aldol/reduction, 8 + 12, and the HWB reaction, 18 + 19 + 6.8 1997 Elsevier Science Ltd.
📜 SIMILAR VOLUMES
The aplyronine C I-CII subunit 4, containing 4 stereocentres and the (E,E)-diene system, was prepared in 7 steps from ethyl ketone (R)-8 using a boron-mediated anti aldol reaction. The corresponding C 15-C27 subunit 5, containing 6 stereogenic centres and an (E)-alkene, was obtained in 10 steps from
An asymmetric synthesis of the C3-C13 segment of rhizoxin is described in which the relative stereochemistry of C7 and C8 is established through a chelation-controlled allylation followed by Mitsunobu inversion, and the pyran ring is constructed by a photochemically initiated 6-exo radical cyclizati
A stereocontrolled synthesis of the C 1 C 9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral b-alkoxy ketones to elaborate the syn-1,3-diol functionality and a