Total Synthesis of Complex Natural Products

复杂天然产物的全合成

• 批准号: 08245103
• 负责人: KUWAJIMA Isao
• 金额: $ 84.35万
• 依托单位: The Kitasato Institute (1998)Tokyo Institute of Technology (1996-1997)
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research on Priority Areas
• 财政年份: 1996
• 资助国家: 日本
• 起止时间: 1996 至 1998
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-08245103/
• 关键词: Complex Natural Products; Taxusin; Taxol; Radicicol; Pironectin; Furaquinocine; Polycavernoside; Enantioselective Total Synthesis; タキソール; ゾアンタミン; タキソ-ル; オーストラリフンジン; ネオカルジノスタチン; 不斉合成; テトロドトキシン; テルペンシン

Total syntheses of complex natural products have been studied in this research group. During this investigation, taxane diterpene was one of major synthetic targets, and enantioselective total syntheses of (+)-taxusin and (-)-taxol have been efficiently achieved based on the B ring cyclization methodology of AC fragment.Other representative natural products synthesized during this research period are radicicol, pironectin, tanabalin, furaquinocine, and polycavernoside.Synthtic studies on α,α-disubstituted α-amino acid sub-structure, zoanthamine/nor-zoanthamine alkaloids, and ravidomycin were also developed.

该课题组研究了复杂天然产物的全合成。在本研究期间，紫杉烷二萜是主要的合成目标之一，基于AC片段的B环环化方法，紫杉醇和(+)-紫杉醇的对映选择性全合成已经得到了有效的实现。在本研究期间合成的其他具有代表性的天然产物有：自由基、吡罗连菌素、他那巴林、呋喃喹啉和海藻糖苷。此外，还开展了α，α-二取代α-氨基酸亚基结构、兽黄胺/去甲基偶氮苯甲胺生物碱和雷维霉素的合成研究。

项目成果

S.Kobayashi: "Synthesis of 2-O-(3-O-Carbamoyl-a-D-mannopyranosyl)-L-glucopyranose : Suger Moiety of Antitumor Antibiotic Bleomycin" Tetrahedron. 53. 10993-11006 (1997)

S.Kobayashi：“2-O-(3-O-氨基甲酰基-a-D-吡喃甘露糖基)-L-吡喃葡萄糖的合成：抗肿瘤抗生素博来霉素的糖部分”四面体。

鈴木啓介: "Total Synthesis of the Furaquinocins"J.Am. Chem.Soc.. 120・45. 11633-11644 (1998)

铃木圭介：“呋喃喹啉的全合成”J.Am.Chem.Soc.120・45（1998）

K.Suzuki: "On the Stereochemistry of Ary C-Glycosides:Unusual Behavior of Bis TBDPS Protected Aryl C-Olivosides" Tetrahedron Lett.37・NO.5. 663-666 (1996)

K.Suzuki：“关于芳基 C-糖苷的立体化学：双 TBDPS 保护的芳基 C-橄榄苷的异常行为”Tetrahedron Lett.37・NO.5 (1996)。

I. Kuwajima: "Enantioselective Total Synthesis of (+)-Taxusin"J. Am. Chem. Soc.. 121, No.13. 3072-3082 (1999)

I. Kuwajima：“( )-紫杉素的对映选择性全合成”J。

M.Isobe: "Pseudoenantiomeric Heteroconjugate Addition Approach for Synthesis of Segment C of Tautomycin" Tetrahedron,. 52・NO.8. 2877-2892 (1996)

M.Isobe：“用于合成互变霉素 C 段的假对映异构体加成法”Tetrahedron，52·NO.8（1996）。