TOTAL SYNTHESIS OF (5R,6S)-DIHETES, (5S,6S)-DIHETES AND (11R,12S)-DIHETES FROM TRICARBONYL ETA-4-BUTADIENYL) IRON(0) COMPLEXES

被引：0

作者：

LELLOUCHE, JP ^{[1
]}

GIGOUBARBEDETTE, A ^{[1
]}

GREE, R ^{[1
]}

机构：

[1] ENSCR,SYNTHESES & ACTIVAT BIOMOLEC LAB,CNRS,URA D1 467,F-35700 RENNES,FRANCE

来源：

BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1992年 / 129卷 / 06期

关键词：

TRICARBONYL (ETA-4-BUTADIENYL) IRON COMPLEXES; OSMYLATION; (5,6)-DIHETES; (11,12)-DIHETE; (14,15)-DIDEHYDRO (11,12)-DIHETE;

D O I：

暂无

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The total synthesis of (5R,6S)-, (5S,6S)- and (11R,12S)-DIHETEs are described starting from the two chiral tricarbonyl (eta4-butadienyl)iron complexes (-)-(2R,5S)-12 and (+)-(2S,5R)-13. This new synthetic approach shows an efficient use of these chiral bifunctionalized iron complexes for the preparation of polyhydroxylated polyenes. The key step of the sequence, ie, the osmylation of a free double bond close to the organonietallic unit, has been studied in detail. The addition Of OsO4 is diastereospecific for the Z-alkenes and highly diastereoselective for the E-alkenes: in both cases, it occurs anti to the Fe(CO)3 group.

引用

页码：605 / 624

页数：20

共 50 条

[41] Enantioselective synthesis of (-)-(5R,6S)-6-acetoxyhexadecan-5-olide via tandem α-aminooxylation-Henry reaction
Pandey, Rachana
Garg, Yuvraj
Prakash, Ranjana
Pandey, Satyendra Kumar
ARKIVOC, 2018, : 20 - 27
[42] SYNTHESIS OF (-)-(R)-4-HYDROXY-BETA-IONONE AND (-)-(5R,6S)-5-HYDROXY-4,5-DIHYDRO-ALPHA-IONONE FROM (-)-(S)-ALPHA-IONONE
HAAG, A
ESCHENMOSER, W
EUGSTER, CH
HELVETICA CHIMICA ACTA, 1980, 63 (01) : 10 - 15
[43] Stereoselective total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (-)-(6S,2′S)-epi cryptocaryalactone
Sabitha, Gowravaram
Bhaskar, V.
Reddy, S. Siva Sankara
Yadav, J. S.
TETRAHEDRON, 2008, 64 (44) : 10207 - 10213
[44] Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F
Akita, Hiroyuki
Iwaki, Yuki
Kato, Keisuke
Qi, Jianhua
Ojika, Makoto
TETRAHEDRON-ASYMMETRY, 2007, 18 (04) : 513 - 519
[45] Synthesis and Herbicidal Activity of [3R*,5S*,6S*]-3-Benzyloxy-5-methoxy-1, 7-dioxaspiro[5.5]undecane and [3R*,5S*,6S*]-3-Methoxy-5-benzyloxy-1, 7-dioxaspiro[5.5]undecane
Brimble, M. A.
Johnston, A. D.
Furneaux, R. H.
Journal of Organic Chemistry, 63 (03):
[46] (2S,3R,4S,5R,6S,7R,8R,9S)-1,2,3,4,5,6,7,8,9-NONAACETOXYDECANE
LEWINSKI, K
MARSHALL, JA
BEAUDOIN, S
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1994, 50 : 1366 - 1368
[47] (6S)-2-tert-Butyl-6-[(4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol
Anderson, Alexander E.
Edler, Kate L.
Parrott, Raleigh W., II
Hitchcock, Shawn R.
Ferrence, Gregory M.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O902 - U2920
[48] The first stereoselective total synthesis of (3S,4R)-dihydroxy-(6S)-undecyl-α-pyranone and total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide
Sabitha, Gowravaram
Nayak, Sambit
Bhikshapathi, M.
Yadav, J. S.
TETRAHEDRON LETTERS, 2009, 50 (38) : 5428 - 5429
[49] Total synthesis of (3R,5R) and (3R,5S)-sonnerlactones
Sanaboina, Chakrapani
Chidara, Sridhar
Jana, Samaresh
Eppakayala, Laxminarayana
TETRAHEDRON LETTERS, 2016, 57 (16) : 1767 - 1770
[50] Conformational and electronic properties of the two cis (5S,6R) and (5R,6S) diastereoisomers of 5,6-dihydroxy-5,6-dihydrothymidine: X-ray and theoretical studies
Jolibois, F
Voituriez, L
Grand, A
Cadet, J
CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (01) : 298 - 305

← 1 2 3 4 5 →