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Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol

✍ Scribed by J.S. Yadav; Sk. Samad Hossain; Debendra K. Mohapatra

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
505 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11.

📜 SIMILAR VOLUMES

Synthesis of the C15–C27 portion of vent
Synthesis of the C15–C27 portion of venturicidins: a formal total synthesis of venturicidin X
✍ Keiji Tsunashima; Mitsuaki Ide; Hiroshi Kadoi; Aya Hirayama; Masaya Nakata 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 84 KB

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

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## 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