寄稿論文 多環状エーテル系天然物の合成戦略 | 東京化成工業
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- ひでか しげまつ
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1 Gymnodinium breve Gambierdiscus toxicus 4 trans 1 Nicolaou Rainier CTX3C
2 C A K B C J D E F I G K J 1 I G Na 3 S F A B C D E C B A Na 3 S D C 2 3 W X Y V Z U A' T F' E' D' C' B' S R 4 Q P Na 3 S B C D E F G I J K N A S 3 Na L M trans iii i Baldwin ii ii iii
3 n R 1 ii R 2 n R 1 n R 1 R 2 R 2 i trans n R 2 iii R 1 5a 7a 5a 7a Ag 2 C Zn(Ac) b 7b 9b 1 4 Ac X 5a: X=S 2 5b: X=S 2 C 2 Cl Zn(Ac) 2 Ac- 2 reflux, 6 h 50 C, 24 h 50 C, 4 h R 75% (after acetylation) 13% (SM 67%) 85% (R=Ac: 8%, R=: 77%) 6 Zn(Ac) 2 X Ac Ac- 2 R 8 7a: X=S 2 7b: X=S 2 C 2 Cl reflux, 8 h 80 C, 6 h 80 C, 3.5 h 95% (R=Ac: 53%, R=: 42%) 0% (SM 60%) 87% (R=Ac:19%, R=: 68%) Ac X 9a: X=S 2 9b: X=S 2 C 2 Cl Zn(Ac) 2 Ac C, 8 h rt, 4 d rt, 26.5 h 50 C, 2 h without Zn(Ac) 2 R Ac 10 90% (R=) 19% (R=) (SM 64%) 92% (R=) 90% (R=Ac:10%, R=: 80%)
4 Ms anti - axial Zn(Ac) 2 aq Ac reflux, 5 min R 89% (R=, 84%; R=Ac, 5%) R Zn(Ac) 2 aq Ac C Ms reflux, 10 min syn - axial 58% (R=, 49%; R=Ac, 9%) 9% Zn 2+ ne Ms 2 oxonium ion antiperiplaner ne Ms Zn(Ac) 2 aq Ac C Ms reflux, 1 hr anti - equatorial 28% 50% ne Zn(Ac) 2 aq Ac C Ms reflux, 1 hr syn - equatorial 77% 22% ne Ms 2 ii R 1 = R 1 = Nicolaou i R 1 =, R 2 = C 2 trans iii 2 11 R = 12 R = 12:13 = 1:1 CR PPTS C 2 Cl 2, rt CR C B CR R= R=Ph Yield 86% 86% 12 : : : 0
5 14 14 CSA PPTS Na DMS trans regio-controller 11 R = Ph 12 R = Ph 5-exo cf. 5-exo 5-exo 6-endo CPh CSA (PPTS), C 2 Cl 2 or Na, DMS CPh 6-endo 6-endo Gymnodinium breve 2 Z α 2 ii iii R 1 = Sharpless Zn(Ac) 2 19 α 20 CSA 21 Z 22 TMSTf C 2 =C(C 2 Ac)C 2 TMS β-axial Mn 2 2
6 18 Ac 1) ClC 2 S 2 Cl 2) Zn(Ac) 2 aq. Ac, 80 C 3) K 2 C 3, Double ring-expansion 61% (3 steps) D 19 C R D CPh C B Ac CSA endo-cyclization of styrylepoxide R D C CPh D R C B A 22 1) TMSTf TMS Ac 2) K 2 C 3 D 3) Mn 2 Direct introduction of C-4 unit 2 C B A C C- C-C iv C-C vi vi C-C β vii vii viii vii vi viii iv AIBN Bu 3 Sn vii trans vi cis cis:trans = 65:35
7 iv v C 2 R viii vii C 2 R C 2 R vi trans 23 Michael TF syn trans syn trans 27 Sm(III) A-1 C-C A-2 A B 1) N- morpholine S C 2 Et C 2 Et C S 2) I, aq. CN 87% TF, 0 C, 10 min 92% C 2 Et C C 2 Et, TF rt, 10 min 84% 27 Sm I2 Et Sm I2 Et Et A-1 A-2 B
8 trans Sm(III) MPA MPA 24 TF-MPA (3:1) syn cis anti trans syn cis 30 MPA Sm C D E C 2 Et C, TF-MPA (3:1) -78 C, 30 min C 2 Et + C 2 Et (56%) 29 (17%) 26 C C 2 Et, TF-MPA (2:1) rt, 10 min 84% 30 C 2 Et MPA Et C 2 Et Et C (MPA) n D (MPA) n E (MPA) n trans 25 DIBA
9 C 2 Et 1) DIBA 2) S(C 2 ) 3 S S BF 3 -Et 2 99% S 1) N- morpholine C 2 Et 2) I, aq. CN 90% C C 2 Et TF, C 2 Et 86% ) DIBA 2) S(C 2 ) 3 S BF 3 -Et 2 3) N- morpholine C 2 Et 4) I, aq. CN 75% C 2 Et C 2 Et C TF, 83% trans ) DIBA 2) S(C 2 ) 3 S 3) C 2 Et 4) I C C2 Et 86% C 2 Et 27 73% C 2 Et C 2 Et C TF, 88% trans diaxial 44 ' ' 45 diaxial F diaxial
10 Ph C n n C 2 Et C 2 Et Ph 40: n=1 or 2 41 C 2 Et C 2 Et n n 42: n=1 or 2 43 Ph Et 2 C C' 44 TF, 99% Ph Et Et 2 C Ph D' C' Sm I 2 45 F diaxial S mi 2 C 2 46 Michael S S S 46 S 1) C 2 Et 2) I, aq CN 90% C C Et 2 C C 2 Et 47 TF, 84% Et 2 C C 2 Et 48 1) DIBA 2) S(C 2 ) 3 S 3) C 2 Et 4) I 42% Et 2 C C 49 C C 2 Et TF, 77% Et 2 C C 2 Et 50
11 ix x xi xii trans xiii xii xiv xv ab initio xii P ix + X P x P xv: 28.7 kj/mol xi P xiv: 57.4 kj/mol xii: 0.0 kj/mol xiii trans C 2 Cl 2 CSA C() TMSTf Et 3 Si trans 56 51
12 TBS Li Tf + TBS TF-MPA 94% TBS TBS 53 Ru 2, NaI 4 CCl 4 -CN- 2 (2:2:3) rt, 21 h 84% TBS CSA, C() 3 Et 3 Si, TMSTf -C 2 Cl 2 C 2 Cl 2, rt, 1 h reflux, 26 h 98% TBS 100% rans ' ' ' ' '
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