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1 Short Lit Jonathan A. Brekan a Department of Chemistry, orthwestern University, 2145 Sheridan Road, 60208, Evanston, Illinois, United States of America
2 Citronellal Monoterpenoid distillate of Cymbopogan antifungal typically isolated as a non-racemic mixture of R and S isomers
3 Citronellal Monoterpenoid distillate of Cymbopogan antifungal typically isolated as a non-racemic mixture of R and S isomers Annual production of citronella oil (40-50%citronellal) is ~2300 metric tons. ~2000 tons of (R)-citronellal produced per year.
4 Synthesis of ( )-menthol (+)-neoisoisopulugol 5% (+)-isoisopulugol 15% (+)-neoisopulugol 19% ( )-isopulugol 61% 2 carbonyl-ene ( )-isopulugol ( )-menthol hloff, G. Tetrahedron Letters, 1960, 1(32), 10-14
5 Takasago Corporation in Japan 1984 A Classic Synthesis - Chapter 22, nthol n-buli (cat.) Li Et 2 Et 2 [Rh((S)-BIAP)(CD) Cl 4 (cat.) Et 2 myrcene Et 2 (telomerization) diethylgeranylamine 100 o C (ca. 100%) citronellal (R,E)-diethylenamine R P * Rh R 2 P Telomerization From Wikipedia, the free encyclopedia * P P suprafacial transfer of from Rh to C3 Rh R 2 (R)-menthol Telomerization is a radical polymerization reaction where a chain transfer limits the size of the oligomer molecule product the telomer.[1][2] Telomerization requires a telogen to react with at least one unsaturated taxogen molecule. [2] Fluorotelomers are an example.
6 A Divergent Approach to the Diastereoselective Synthesis of Several Ant-Associated Iridoids Joel S. Beckett, James D. Beckett, and John E. offerberth* Department of Chemistry, Kenyon College, Gambier, hio epetalactol 4 steps Actinidine 3 steps C C Dolichodial 5 steps Isoirdomyrmecin 11 steps Dihydronepetalactone 6 steps
7 A Divergent Retrosynthesis C C R R 1 C C C citronellal
8 eopetalactol C Se 2 (3 mol %) t-bu salicylic acid DCM, rt 40-50% + C C IBX, DMS 80-90% R Se R Se R + 2 R Se o + Se
9 eopetalactol C Se 2 (3 mol %) t-bu salicylic acid DCM, rt 40-50% + C C IBX, DMS 80-90% Ph Et 2, rt, 24 hr 84% Ph Ph Ts TF (wet) 84% neopetalactol α/β 1:10 Ph Schreiber, S. L.; yers,. V.; Wiberg, K. B. J. Am. Chem. Soc. 1986, 108, 8277
10 Actinidine C 2, Ts TF 70% Dolichodial Ph BS 72% Br Ph Br Br + Ph (3:4) Ph t-buk, 50 o C TF, Cl 87% C C
11 Dihydronepetalactones A and B 2, Pd/C 95% Ag 2 C 3 /celite 88% Ag 2 C 3 /celite 70% 2, Pd/C 95%, 95:5 dr
12 Ph 1) 2, Pd/C, Et 2) 1,2-ethandithiol, BF 3 Et 2 3) BnBr, a, n-bu 4 I (cat.) 80% S S Bn 1) CA, C, ab 4 2) Ac 2, Py, DMAP 66% Ac Bn 1) Pd/C, 2, Et 2) RuCl 3, ai 4, CCl 4 C 2 Ac Ts, Et quant. Isoiridomyrmecin epetalactol 4 steps C C Dolichodial 5 steps Actinidine 3 steps Dihydronepetalactone 6 steps
13 Tetrahedron Letters 51 (2010) Contents lists available at ScienceDirect Tetrahedron Letters journal homepage: locate/tetlet Total synthesis of (+)-aspermytin A Atsushi Inoue, Makoto Kanematsu, Masahiro Yoshido, Kozo Shishido* Gradute School of Pharmaceutical Sciences, The University of Takushima aspermytin A equisetin
14 Retrosynthesis C C R C R C (S)-citranellal
15 C (C 2 ) 2 pts, benzene 3, then ab 1) 0.5 M Cl 2) TBSCl imidazole, DMAP C TBS
16 Cl Cl B C TBS TMSCl (6 equiv) CrCl 2 (0.6 equiv) Mn (6 equiv) LiI (4 equiv) TBS B TBS R RCCl C CrX 2 2 CrX 2 TBS R 1 C Tf CrX 2 4 CrX 2 2 CrX CrX 3 R 1 CrX 2 R (X 2 Cr) 2 2 MnX 2 2 Mn (TMS) 2 2 TMSCl R 1 R Takai *, K.; Kunisada, Y.; Tachibana, Y.; Yamaji,.; akatani, E. Bull. Chem. Soce. Jpn. 2004, 77,
17 Cl Cl B C TBS TMSCl (6 equiv) CrCl 2 (0.6 equiv) Mn (6 equiv) LiI (4 equiv) TBS B Br TBDPS Pd 2 (dba) 3 CCl 3, PPh 3 1 a 1) Swern, 86% 2) WE, 99% C 2 Et,then 0.5 Cl 83% over 3 steps TBDPS TBDPS 1) DIBA, 99% 2) Mn 2, quant. TBDPS
18 Conditions C R C R TBDPS + 3 Al (1.5) 78 to hrs 52% (13.5:1) Et 2 AlCl (0.5) 78 to 0 2 hrs 78% (10:1) 2 AlCl (1.5) 78 to hrs 92% (8:1) R vs R
19 R 1) MMCl quant. MM 1) DMP, 94% MM C 2 2) TBAF 2) acl 2 a 2 P Butene 3) C 2 2, 98% (2 steps) MM MM MM C 2 KMDS, 2 (Et) 3 P C 2 + C 2 27% 38%
20 Change of Strategy MM 1) 2, Pd/C, 96% 2)nBu 3 P, o-nitro-phenyl selenocyanate, 30% 2 2 MM 3 MM [] Se 2 PBu 3 MM MM PBu 3 SeAr +C Grieco, P. A.; Gilman, S.; ishizawa, M. J. rg. Chem. 1976, 41, 1485
21 Let s Wrap This Up MM 1) 2, Pd/C, 96% 2)nBu 3 P, o-nitro-phenyl selenocyanate, 30% 2 2 MM 3 MM IBX, DMS MM + 1) Cl 2) DMP icolaou, K.C.; Zhong, Y.L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596 Li, TF 80% TPAP, M 92% LDA 95% aspermytin A [α] 28 d = +7.6 ; lit. [α]25 d = +1.2 Deguest, G.; Bischoff,* L.; Fruit, C.; Marsais, F. rg. Lett. 2007, 9, 1165
22 Citronellal
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