[1]胡 昆,杨泽华,任 杰.天然产物Quadrone 的全合成进展[J].常州大学学报(自然科学版),2009,(03):73-78.
 HU Kun,YA NG Ze -hua,REN Jie.Progress in Total Synthesis of Natural Product Quadrone[J].Journal of Changzhou University(Natural Science Edition),2009,(03):73-78.
点击复制

天然产物Quadrone 的全合成进展()
分享到:

常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2009年03期
页码:
73-78
栏目:
出版日期:
2009-09-25

文章信息/Info

Title:
Progress in Total Synthesis of Natural Product Quadrone
作者:
胡 昆 杨泽华 任 杰
江苏工业学院化学化工学院, 江苏 常州 213164
Author(s):
HU Kun YA NG Ze -hua REN Jie
School of Chemist ry and Chemical Engineering , Jiangsu Polytechnic University , Changzhou 213164 , China
关键词:
quadrone 抗癌全合成倍半萜
Keywords:
quadrone antitumor total sy nthesis sesquiterpene
分类号:
O 627.52
文献标志码:
A
摘要:
Qu adrone 是土曲霉的代谢产物, 由于其较强的抗癌活性和新颖的四环倍半萜结构, 吸引了众多化学工作者对其全合成展 开研究。此化合物的合成方法较多, 总结了近30 年来该领域的研究进展, 介绍了17 条外消旋及光学纯quadrone 的全合成路 线, 并讨论了其优劣。
Abstract:
Quadrone , a fung al metabo li te f rom Aspergil lus terreus , has mot ivated intense re sea rch ef fo rts by lo ts of chemi st s due to i ts out standing antitumor proper ty and nov el tet racyclic ring sesquiterpene system .Plenty o f metho ds fo r the sy nthesis of quadro ne had been established .In this paper , the pro gress in to tal sy nthesis of quadro ne in the past three decades w as reviewed .Seventeen synthet ic routes of dl -quadrone and optical quadro ne w ere illustrated , and it s pro s and co ns w ere also put fo rw ard respect ively .

参考文献/References:

[1] Ranieri R L , Calt on G J .Qu adrone , A new anti tumor agent f rom aspergi llus terreu s [J] .Tet rahedron Let t ers , 1978 , 19 (6):499 -502 .
[2] Ku pchan S M , Eakin M A , Thomas A M .S t ructure cy tot oxici ty relat ionships among the s esqui terpene t actones [J] .J M ed Chem , 1971 , 14 (12):1 147 -1 150 .
[3] Dani shef sky S J , Vaughan K, Gadw ood R C , et al.T otal S ynthesis of dl-quad ron e [J] .J Am C hem Soc, 1980 , 102 (12):4 262 -4 263 .
[4] Bornack W K , Bhagw at S S , Pont on J , et al.Preparati on of lactone syst em s , Tot al syn thesis of (±) -quad rone [J] .J Am Ch em Soc, 1981 , 103 (13):4 647-4 648 .
[5] Kon K , It o K , Isoe S .Sy nthesi s of (-) -terrecyclic acid A, ab solut e configu rat ion of terrecycli c acid A and quad ron e [J] .Tet rah edron Lett ers , 1984 , 25 (34):3 739 -3 742.
[6] Iw ata C , Yamashi ta M , Aoki S , et al.A f ormal tot al syn thesi s of (±) - qu adrone [J] .Chem Pharm Bull , 1985 , 33 (1):436 -439 .
[7] Magnus P , Principe L M , Slat er M J .St ereospecif ic dicobalt octacarbonyl medi at ed enyne cyclizati on f or th e synthesis of th e cyt otoxic s esqui terpen e (±) -Qu adrone [J] .J Org Chem , 1987 , 52 (8):1 483 -1 486 .
[8] Liu H J , Bru net M L .T otal syn th esi s of natural quad ron e [J] .Can J Chem , 1988 , 66 :528 -530 .
[9] Kende A S , Roth B, Sanfilippo P J , et al.M echam ni sm and regi oi someri c cont rol in Palladium (Ⅱ) -Mediat ed cy cloalkenylati ons , A novel t otal sy nthesi s of (±) -quadrone [J] .J Am Chem S oc, 1982 , 104 (15):5 808 -5 810.
[10] Schlessinger R H , Wood J L , Poss A J , et al.An int ram olecular Diesl -Alder rou te t o racemi c quadrone [J] .J Org Chem , 1983 , 48 :1 146 -1 147 .
[11] Dewanckele J M , Zut t erm an F , Vandew al le M .Sesquit erpene lact on es , A t ot al synthesis of (±) - qu adrone [J] . T et rahed ron , 1983 , 39 (20):3 235 -3 244 .
[12] Imani shi T , Matsui M , Iw at a C , et al.Anomalou s t ran sf ormation of t ricycle
[3 .3 .0 .02 , 8] oct an -3 -ones in to bicycl e
[3 .2 .1] octan -3 -ones , a novel rout e t o (±) - quadrone [J] .J Chem S oc Chem Comm un , 1987 , 57 (10): 1 802 -1 804 .
[13] Fu nk R L , Abelm an M M .Synthesis of b ridged bicycloalkanes via the alicy clic Clai sen rearrangemen t , a new app roach t o quadrone [J] .J Org Chem , 1986 , 51 (16):3 247 - 3 248 .
[14] S ow ell C G , Wolin R L , Lit t le R D.Elect roreductive cycli zati on reacti ons , st ereoselect ion , creation of quaterrnary cent ers in bicyclic f ramew ork s , and a f ormal t ot al s ynthesi s of quadrone [J] .Tet rahedron Let t ers , 1990 , 31 (4):485 -488 .
[15] Burke S D , Murt iashaw C W, S aunders J O , et al.A novel and eff icient ent ry t o (±) -quadrone [J] .J Am Chem S oc , 1982 , 104 (3):872 -874 .
[16] Wender P A , Wolanin D J .T otal syn th esi s of quadrone and t errecyclic acid A [J] .J O rg Chem , 1985 , 50 (22):4 418 - 4 420 .
[17] Erm ol enk o M S , Pipeli er M .A carbohydrat e-based synthetic app roach t o quadrone [J] .T et rahedron Lett ers , 1997 , 38 (34):5 975 -5 976 .
[18] Takeda K , Shim on o Y , Yoshii E .A sho rt -s tep ent ry t o (±) -quad ron e [J] .J Am Chem Soc, 1983 , 105 (3):563 -568 .
[19] Smi th A B Ⅲ , Konopelski J P .Tot al synthesis of (±) - quadrone:as signment of absolu te stereochem ist ry [J] .J Org Chem , 1984 , 49 :4 094 -4 095 .
[20] Pi ers E , M oss N .Thermal rearrangement of di viny lcycl op ropan e syst ems , a new f ormal tot al synthesis of (±) -Quadrone [J] .Tet rahedron Let t ers , 1985 , 26 (23):2 735 - 2 738 .
[21] T oyot a M .S ynthesis of polycycli c compound s empl oying palladium -catalyzed cycloalkenylati on [J] .Yuki Gosei Kagaku Kyokai shi , 2006 , 64 (1):25 -33 .
[22] Wi jeratne E M K , Tu rby vi lle T J , Zhang Z G, et al .Cyt ot oxi c const ituent s of A spergil lus terreus f rom the rhizosph ere of Opunt ia versicol or of th e S onoran Desert [J] .Journal of Natural Products , 2003 , 66 (12):1 567 -1 573 .
[23] St ephens P J , McCann D M , Devlin F J, et al.Determination of the absolut e configurations of natural product s via densit y funct ional theory calculat ions of optical rotat ion , electronic ci rcular di chroism , and vibrational ci rcular dichroism :the cytotoxi c sesqui terpene natural products quadrone, suberosenone, suberosanone, and suberosenol a acetate [J] .Journal of Natural Product s, 2006, 69 (7):1 055 -1 064 .

备注/Memo

备注/Memo:
作者简介:胡昆(1979 -), 男, 山东兖州人, 博士;联系人:任杰。
更新日期/Last Update: 2009-09-25