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The norcembranoid diterpenoid natural products possess a complex and compact tetracyclic core scaffold, consisting of a functionalized six-or seven-membered ring, along with four to eight adjacent stereogenic centers, and several unstable structural units.The norcembranoid diterpenoids exhibit biological activities such as anti-cancer, anti-inflammatory, and cytotoxicity.We summarize the synthesis progress of norcembranoid diterpenoid natural products in recent years, including scabrolide A,yonarolide, sinulochmodin C,and ineleganolide.
[1] TADROSS P M,STOLTZ B M.A Comprehensive history of arynes in natural product total synthesis[J].Chemical Reviews,2012,112(6):3550-3577.
[2] BRILL Z G,CONDAKES M L,TING C P,et al.Navigating the chiral pool in the total synthesis of complex terpene natural products[J].Chemical Reviews,2017,117(18):11753-11795.
[3] HU Y J,LI L X,HAN J C,et al.Recent advances in the total synthesis of natural products containing eight-membered carbocycles(2009-2019)[J].Chemical Reviews,2020,120(13):5910-5953.
[4] MIN L,HAN J C,ZHANG W,et al.Strategies and lessons learned from total synthesis of taxol[J].Chemical Reviews,2023,123(8):4934-4971.
[5] CRAIG R A,STOLTZ B M.Polycyclic furanobutenolide-derived cembranoid and norcembranoid natural products:biosynthetic connections and synthetic efforts[J].Chemical Reviews,2017,117(12):7878-7909.
[6] ROETHLE P A,TRAUNER D.The chemistry of marine furanocembranoids,pseudopteranes,gersolanes,and related natural products[J].Natural Product Reports,2008,25(2):298-317.
[7] KAMEL H N,SLATTERY M.Terpenoids of Sinularia:chemistry and biomedical applications[J].Pharmaceutical Biology,2005,43(3):253-269.
[8] YAN X,LIU J,LENG X,et al.Chemical diversity and biological activity of secondary metabolites from soft coral genus Sinularia since 2013[J].Marine Drugs,2021,19(6):335-359.
[9] LI G,DICKSCHAT J S,GUO Y W.Diving into the world of marine 2,11-cyclized cembranoids:a summary of new compounds and their biological activities[J].Natural Product Reports,2020,37(10):1367-1383.
[10] LI Y,PATTENDEN G.Novel macrocyclic and polycyclic norcembranoid diterpenes from Sinularia species of soft coral:structural relationships and biosynthetic speculations[J].Natural Product Reports,2011,28(2):429-440.
[11] LI Y,PATTENDEN G.Perspectives on the structural and biosynthetic interrelationships between oxygenated furanocembranoids and their polycyclic congeners found in corals[J].Natural Product Reports,2011,28(7):1269-1310.
[12] TSENG Y J,AHMED A F,DAI C F,et al.Sinulochmodins A-C,three novel terpenoids from the soft coral Sinularia lochmodes[J].Organic Letter,2005,7(17):3813-3816.
[13] SHEU J H,AHMED A F,SHIUE R T,et al.Scabrolides A-D,four new norditerpenoids isolated from the soft coral Sinularia scabra[J].Journal of Natural Products,2002,65(12):1904-1908.
[14] IGUCHI K,KAJIYAMA K,YAMADA Y.Yonarolide:a new marine norditerpenoid possessing a novel tricyclic skeleton,from the Okinawan soft coral of the genus,Sinularia[J].Tetrahedron Lettert,1995,36(48):8807-8808.
[15] THAO N P,NAM N H,CUONG N X,et al,Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima[J].Bioorganic & Medicinal Chemistry Letters,2013,23(1):228-231.
[16] TRUAX N J,AYINDE S,VAN K,et al.Pharmacophore-directed retrosynthesis applied to rameswaralide:synthesis and bioactivity of Sinularia natural product tricyclic cores[J].Organic Letters,2019,21(18):7394-7399.
[17] HAFEMAN N J,LOSKOT S A,REIMANN C E,et al.The total synthesis of (-)-scabrolide A[J].Journal of the American Chemical Society,2020,142(19):8585-8590.
[18] NEISES B,STEGLICH W.Simple method for the esterification of carboxylic acids[J].Angewandte Chemie:International Edition,1978,17:522-524.
[19] MENG Z C,FÜRSTNER A.Total syntheses of scabrolide A and nominal scabrolide B[J].Journal of the American Chemical Society,2022,144(4):1528-1533.
[20] SHIINA I,HASHIZUME M,YAMAI Y,et al.Enantioselective total synthesis of octalactin A using asymmetric aldol reactions and a rapid lactonization to form a medium-sized ring[J].Chemistry:A European Journal,2005,11(22):6601-6608.
[21] SERRANO R,BOYKO Y D,HERNANDEZ L W,et al.Total syntheses of scabrolide A and yonarolide[J].Journal of the American Chemical Society,2023,145(16):8805-8809.
[22] SCHEIDT K A,BANNISTER T D,TASAKA A,et al.Total synthesis of (-)-bafilomycin A1[J].Journal of the American Chemical Society,2002,124(24):6981-6990.
[23] PENG C,GUO Q P,XU G X,et al.Divergent synthesis of scabrolide A and havellockate via an exo-exo-endo radical cascade[J].Journal of the American Chemical Society,2024,146(21):14422-14426.
[24] LI Y,PATTENDEN G.Biomimetic syntheses of ineleganolide and sinulochmodin C from 5-episinuleptolide via sequences of transannular Michael reactions[J].Tetrahedron,2011,67(51):10045-10052.
[25] TUCCINARDI J P,WOOD J L.Total syntheses of (+)-ineleganolide and (-)-sinulochmodin C[J].Journal of the American Chemical Society,2022,144(44):20539-20547.
[26] ZHANG Y P,DU S F,MA Y,et al.Structure-unit-based total synthesis of (-)-sinulochmodin C[J].Angewandte Chemie:International Edition,2024,63(2):e202315481.
[27] GAO J H,RAO P R,XU K X,et al.Total synthesis of (-)-rhodomollanol A[J].Journal of the American Chemical Society,2020,142(10):4592-4597.
[28] NICOLAOU K C,ESTRADA A A,ZAK M,et al.A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide[J].Angewandte Chemie:International Edition,2005,44(9):1378-1382.
Basic Information:
China Classification Code:TQ460.1
Citation Information:
[1]ZENG Shanji,LI Di,LONG Ai ,et al.Synthesis Progress in Norcembranoid Diterpenoids[J].Chemistry & Bioengineering,2026,43(07):10-17.
Fund Information:
国家自然科学基金项目(700237231108); 贵州省基础研究(自然科学)项目(ZK[2021]039)
2026-07-06
2026-07-06