We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step fol
Synthesis of the C15–C27 portion of venturicidins: a formal total synthesis of venturicidin X
✍ Scribed by Keiji Tsunashima; Mitsuaki Ide; Hiroshi Kadoi; Aya Hirayama; Masaya Nakata
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 84 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The C15-C27 portion of venturicidin X was prepared using substitution reactions of alkyl trifluoromethanesulfonates with a vinylmetal compound followed by homogeneous hydrogenation. Together with our previous synthesis of the C1-C14 portion of venturicidin X, a formal total synthesis of venturicidin X was completed.
📜 SIMILAR VOLUMES
## Abstract Chain extension of an aldehyde by two “propionate” units has been attained by stereoselective allylboration with the chiral 1‐methylbutenyl boronate 3 to give, e.g., the homoallylic alcohol 6, followed by a regioselective hydroboration/carbonylation procedure to give, e.g., the epimeric
The C15-C27 segment 2 of the aglycone ,$ of venturicidins A and B was synthesized and then total synthesis of 3 was accomplished via intramolecular Wittig-Horner reaction of the ester from 2 and the previously synthesized Cl-Cl4 segment 1. In the preceding paper, the synthesis of the Cl-Cl4 segment