Corey-Fuchs reaction enabled synthesis of natural products: a review

Abstract

Natural products can be derived from a vast array of animals, plants and microorganisms and are generally characterized by a wide spectrum of bioactive properties such as anti-viral, anti-cancer, anti-inflammatory and anti-bacterial properties. Synthesis of natural products is of paramount importance in various fields including medicine, biotechnology and agriculture. The Corey-Fuchs reaction, also known as the Ramirez Corey-Fuchs reaction, is a pivotal organic transformation and plays a significant role in the synthesis of intricate natural products and their analogues. This review article highlights the development of the Corey-Fuchs reaction in recent years towards the synthesis of complex natural products including polyketides, alkaloids, terpenoids and peptides.

Scheme 1. General reaction of Corey–Fuchs protocol.

Scheme 2. General mechanism for Corey–Fuchs reaction involving the synthesis of terminal alkyne.

Fig. 1. Structure of some biological important natural products having Corey–Fuchs reaction as main step in total synthesis.

Scheme 3. Total synthesis of chatenaytrienin-4 27 by Adrian and Stark.

Scheme 4. Total synthesis of tetrangulol 38 by Ngwira and coworkers.

Scheme 5. Total synthesis of C16–C28 fragment of hemicalide 48 by MacGregor and coworkers.

Scheme 6. Total synthesis of key intermediate of the actinoallolide A (+)-60 by Ohista and coworkers.

Scheme 7. Total synthesis of putative orevactaene 74 & epipyron A 76 by Preindl and coworkers.

Scheme 8. Total synthesis of (−)-dactylolide 85 by Tanaka and coworkers.

Scheme 9. Total synthesis of polyketide fragment of the natural product seragamide A 99 by Lang and Lindel.

Scheme 10. Total synthesis of (−)-enigmazole A 108 & (−)-15-O-methylenigmazole 109 by Sakurai and coworkers.

Scheme 11. Total synthesis of metacridamide B 120 by Sharma and coworkers.

Scheme 12. Total synthesis of veramycin A 134, NFAT-133 126 & TM-123 131 by Dardić and coworkers.

Scheme 13. Total synthesis of (±)-parvistilbine B 148 & (±)-stemenone B 147 by Kozlowski and coworkers.

Scheme 14. Total synthesis of aigialomycin D 160 by Sudhakar and coworkers.

Scheme 15. Total synthesis of C22–C40 fragment 173 of azaspiracids by Zhang and coworkers.

Scheme 16. Total synthesis of tetradecapentaenoic acid amide 178 by Kolodiazhna & Kolodiazhnyi.

Scheme 17. Total synthesis of tetradecapentaenoic acid derivatives 178 & 186 by Kolodiazhna & Kolodiazhnyi.

Scheme 18. Total synthesis of (−)-chelonin A 196 by Gunawana and coworkers.

Scheme 19. Total synthesis of schwarzinicines A–D 208–211 by Annapurna and coworkers.

Scheme 20. Total synthesis of xestospongenyne 218 by Gong and coworkers.

Scheme 21. Total synthesis of (5Z,9Z)-eicosa-5,9-dienoic acid 220 by Adrian and Stark.

Scheme 22. Total synthesis of resolvin D4 232a and its 17(R)-hydroxy-epimer 232b by Nshimiyimana and coworkers.

Scheme 23. Total synthesis of (−)-gummiferol 242a & (+)-gummiferol 242b by Sarabia and coworkers.

Scheme 24. Total synthesis of atractylodinol 248 by Kraus and coworkers.

Scheme 25. Total synthesis of distaminolyne A 258 by Dumpala and coworkers.

Scheme 26. Total synthesis of petrosiol B 268 & petrosiol D 269 by Geng and coworkers.

Scheme 27. Total synthesis of Waihoensene 279 by Lee and coworkers.

Scheme 28. Route leading towards the total synthesis of shagene A 289 by Bai and coworkers.

Scheme 29. Total synthesis of houttuynoid B 301 by Kerl and coworkers.

Scheme 30. Total synthesis of nepetoidin B 306 by Yao and coworkers.

Scheme 31. Total synthesis of haliclamide 315 by Gahalawat and coworkers.

Scheme 32. Total synthesis of fusaramin 328 by Kimishima and coworkers.