๐”– Bobbio Scriptorium
โœฆ   LIBER   โœฆ

Total synthesis of (+)-crocacin A

โœ Scribed by Tushar K. Chakraborty; Pasunoori Laxman

Book ID
104253845
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
172 KB
Volume
44
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

โœฆ Synopsis

Total synthesis of the potent antifungal and cytotoxic agent (+)-crocacin A is described. The crucial (Z)-5,6-enoic amide moiety in this molecule was built by stereoselective partial reduction of a skipped diyne precursor. The diene, thus obtained, was transformed into a silyl epoxide that was regioselectively opened with an azide ion to furnish an a-azido-b-hydroxyalkylsilane intermediate. Peterson elimination of this b-hydroxysilane component in the final step resulted in the formation of the (Z)-8,9-enamide moiety of the molecule leading to a successful completion of its total synthesis.

๐Ÿ“œ SIMILAR VOLUMES

Total Synthesis of (+)-Crocacin A.
Total Synthesis of (+)-Crocacin A.
โœ Tushar K. Chakraborty; Pasunoori Laxman ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› John Wiley and Sons โš– 56 KB ๐Ÿ‘ 2 views
Total Synthesis of (+)-Crocacin A (I).
Total Synthesis of (+)-Crocacin A (I).
โœ John T. Feutrill; Mark A. Rizzacasa ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› John Wiley and Sons โš– 57 KB ๐Ÿ‘ 2 views
Total Synthesis of (+)-Crocacin C
Total Synthesis of (+)-Crocacin C
โœ Feutrill, John T.; Lilly, Michael J.; Rizzacasa, Mark A. ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› American Chemical Society ๐ŸŒ English โš– 54 KB