摘要
本论文是B族维生素—(+)-生物素和辅酶Q_(10)的不对称全合成及基相关反应的研究,主要分以下四个部分:
第一部分综述了半个多世纪以来国内外学者沿仿Roche公司的Sternbach合成法开发(+)-生物素合成路线所取得的各项研究进展,包括:1、(+)-生物素关键手性砌块(3aS,6aR)-内酯的制备;2、由(3aS,6aR)-内酯制备(3aS,6aR)-硫内酯方法;3、(3aS,6aR)-硫内酯C_4位的五碳侧链引入;4、双苄生物素脱苄。指出了Sternbach合成仍不失为工业全合成(+)-生物素行之有效的途径,且高立体选择性合成(3aS,6aR)-内酯和高效、简洁引入侧链依然是该技术改进的关键所在。
第二部分以金鸡纳生物碱(奎尼和奎尼丁)为先导化合物,分别对其C_6、C_9位进行结构修饰,设计合成了16个金鸡纳生物碱衍生物(其中9个为新化合物)。通过16个催化剂对内消旋环酸酐3不对称甲酯化的研究,以及反应条件(反应物/催化剂配比、溶剂、温度、亲核试剂)的优化,高收率高立体选择性地合成了(+)-生物素关键手性砌块(3aS,6aR)-内酯。利用阴离子交换树脂分散的纳米钯(Pd@D296)作为催化剂成功地在(3aS,6aR)-硫内酯8的C_4位经改良的Fukuyama偶联反应一步导入羧丁基侧链,续行离子氢化还原立体专一地建立生物素的第三个手性中心。开发了一条具有潜在工业化应用价值的(+)-生物素不对称全合成路线。
第三部分以辅酶Q_(10)的全反式癸异戊烯侧链构建的方式综述了近五十年来辅酶Q_(10)化学合成的研究进展。指出了以国内丰富来源的茄呢醇为原料通过侧链延长策略构建全反式癸异戊烯侧链是化学合成辅酶Q_(10)最为有效的方法。
第四部分开发了一条以茄呢醇为原料以C_5+C_(45)构筑全反式癸异戊烯侧链为关键合成策略的高立体选择性合成辅酶Q_(10)的新途径。将SeO_2高区域选择性氧化烯丙位末端法创造性地应用于辅酶Q_1侧链末端基团功能化,完成高效偶联后一锅脱除苄基和砜基,实现了高立体选择性辅酶Q_(10)的合成。另外,采用C_0+C_(50)策略,通过氢醌脂肪酸单酯与癸异戊烯醇直接缩合法研究,简便快捷地合成了辅酶Q_(10),为某些具有生理活性并含有多烯长链的类似化合物合成提供技术平台。
此外,本论文通过IR、~1H NMR、~(13)C NMR、MS、CD和X—单晶衍射对涉及的中间体进行了结构鉴定,通过~1HNMR和手性HPLC对相关的对映异构体过量(ee)进行测定。
In this thesis, we have developed two high stereo- and region-selective total synthesis of (+)-biotin and coenzyme Q_(10).
In chapter 1, the development of Roche's Sternbach total synthesis of (+)-biotin over the past six decades have been reviewed, including: 1) the preparation of the key chirl building block-(3aS, 6aR)-lactone; 2) the conversion of (3aS, 6aR)-lactone into (3aS, 6aR) - thiolactone; 3) the introduction on C_4 position of (3aS, 6aR) - thiolactone; 4) the Debenzylation of (+)-debenzylbiotin. As mentioned, the high stereoselective synthesis of (3aS, 6aR)-lactone and the convenient installation of carboxybutyl chain is still a challenge along the significant progress of Roche's Sternbach total synthesis of (+)-biotin.
In chapter 2, the modifications of C_6 and C_9 -position in Cinchona Alkaloids (quinine and quinidine) have been made to lead to the identification of 16 Cinchona derivatives for our asymmetric alcholysis of meso-cyclic anhydride in the total synthesis of (+)-biotin as organocatalysts. The different conditions, such as solvents, temperature, ratios of catalysts and alchols were investigated, the optimized reaction will aim to the high enantioselectivity preparation of (3aS, 6aR)-lactone, a key chiral intermediate for the total synthesis of (+)-biotin. An improved Fukuyama-type cross coupling reaction employing palladium nanoparticles immobilized anion exchang resin D296 (Pd@D296) was used in a one-step introduction of carboxybutyl chain onto (3aS, 6aR) - thiolactone. The third chiral center of (+)-biotin was established creatively by an ionic hydrogenation of 9 under mild reaction conditions. These promising results pave a way for exploring a practical and high steroselectivty total synthesis of (+)-biotin.
In chapter 3, a view showing the considerable efforts toward the chemical synthesis of Coenzyme Q_(10) from the first synthesis in 1959 is presented, including the strategies based on direct elaboration of decaprenyl side chain, the elongation of polyprenyl side chain and the total synthesis. The construction of liner polyprenoid chains represents a major synthetic challenge and the development of a convenient approach for the chemical synthesis of Coenzyme Q_(10) is still in demand.
In chapter 4, An improved route to coenzyme Q_(10) via the C_5+C_(45) approach starting from commercially available coenzyme Q_1 and solanesol was investigated, the key steps in this synthesis are the SeO_2-mediated oxidation of the protected isoprenylhydroquinone into the terminal trans-allylic alcohol without the formation of undesired stereoisomer and one-pot reductive elimination of the phenylsulfonyl and dibenzyl groups using lithium naphthalenide. In addition, another route to coenzyme Q_(10) based on the C_0+C_(50) strategy employing all-trans-decaprenyl alcohol and 4-hydroxy-2,3-dimethoxy-6-Methylphenyl acetate(4) has been developed. These research results provide good foundation for exploring the synthesis of natural products in possession of liner polyprenoid chains.
The structure of all synthesized compounds were charactered by IR、~1H NMR、~(13)C NMR、MS、CD, the absolute configuration of some now compounds were futher comfirmed by X-ray crystal structure analysis respectively.
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