Asymmetric total synthesis of highly symmetric squalene-derived cytotoxic polyethers

Chirality

Volumn 14, Issue 7, 2002, Pages 578-586

  Morimoto, Yoshiki ^a   Kinoshita, Takamasa ^a   Iwai, Toshiyuki ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Biogenesis; Glabrescol; Longilene peroxide; Rhenium(VII) oxide; Sequential cascade cyclizations; Tetrahydrofuran; Teurilene; Two directional synthesis; Vanadium

Indexed keywords

NATURAL PRODUCT; POLYETHER; RHENIUM; SQUALENE DERIVATIVE; VANADIUM;

CATALYSIS; CHELATION; CHIRALITY; CONFERENCE PAPER; CYCLIZATION; CYTOTOXICITY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

ALCOHOLS; ETHERS; MODELS, CHEMICAL; SQUALENE; TEMPERATURE;

EID: 0036084915     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10083     Document Type: Conference Paper

References (35)

1. Biosynthesis of sterols, steroids, and terpenoids. I. Biogenesis of cholesterol and the fundamental steps in terpenoid biosysnthesis
2. Unified stereochemical model of polyether antibiotic structure and biogenesis
3. The biosynthesis of marine natural products
4. Annonaceous acetogenins: Recent progress
5. Enshuol, a novel squalene-derived pentacyclic triterpene alcohol from a new species of the red algal genus Laurencia
6. Teurilene and thyrsiferyl 23-acetate, meso and remarkably cytotoxic compounds from the marine red alga Laurencia obtusa (Hudson) Lamouroux
7. A new squalene-type triterpene from the woods of Eurycoma longifolia
8. Squalene derivatives from Eurycoma longifolia
9. Glabrescol. A unique squalene-derived penta-THF diol from Spathelia glabrescens (Rutaceae)
10. Diastereoselective two-directional synthesis and cation transport ability of the central tristetrahydrofuranyl unit of meso polyether glabrescol as naturally occurring podand
11. Biomimetic membrane transport: Interesting ionophore functions of naturally occurring polyether antibiotics toward unusual metal cations and amino acid ester salts
12. A new family of cationbinding compounds: Threo-α,ω-poly(cyclooxalkane)diyl
13. Oligo-THF peptides: Synthesis, membrane insertion, and studies of ion channel activity
14. Total synthesis of the meso-triterpene polyether teurilene
15. Asymmetric synthesis of achiral molecules: Meso selectivity
16. Synthesis and biomimetic rearrangement of a chiral diterpene dioxide
17. What is the structure of glabrescol? Stereoselective synthesis of reported glabrescol
18. s-symmetric diastereomers compel structural revision
19. 2-symmetric pentacyclic oxasqualenoid
20. Highly diastereoselective cyclizations of bishomoallylic tertiary alcohols promoted by rhenium (VII) oxide. Critical steric versus chelation effects in alkoxyrhenium intermediates
21. Effective combination of two-directional synthesis and rhenium(VII) chemistry: Total synthesis of meso polyether teurilene
22. 2 symmetric relationships
23. Synthetic routes to 2,5-disubstituted tetrahydrofurans
24. The total synthesis of (+)-ionomycin
25. Syn-Oxidative polycyclizations of hydroxypolyenes: Highly stereoselective and potentially biomimetic syntheses of all-trans-polytetrahydrofurans
26. Oxidative cyclization of 5-hydroxyalkenes with rhenium oxide, utilizing a co-oxidant. IV
27. Two-directional synthesis and its use in natural product synthesis
28. Multiple bonds between transition metals and main-group elements. 124. Structures and reactivity of acylperrhenates
29. Table of conformational energies
30. The oxidative spirocyclization of 2-(ω-(OH)-alkyl) cyclic enol ethers by rhenium (VII)-oxide
31. Rules of stereoselectivity in tandem oxidative polycyclization reaction with rhenium(VII) oxides
32. Stereospecific synthesis of 2,7-dimethyl-trans,trans-2,6-octadiene-1,8-dial, a tail-to-tail all-trans bifunctional isoprenoid synthetic unit. A convenient synthesis of squalene
33. Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization
34. Total synthesis and determination of the absolute configuration of (-)longilene peroxide