synthesis of amphotericin b (k. c. nicolaou 1987)

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SYNTHESIS OF AMPHOTERICIN B (K. C. NICOLAOU 1987) In ten siv e P ro g ra m 31388-IC -11-2005-1-G R -ER A SM U S-IPU C -1 S Y N A P S : S y n th e sis a n d R e tro sy n th e sis in th e C hem istry o f N atu ra l P ro d u cts N A T U R A L P R O D U C T CHEM ISTRY M o d u le 2 R e tro sy n th e tic A p p ro ach es T o w a rd s th e S y n th e sis o f N atu ra l P rod u cts P ro f. H . E . K aterin op ou los E d u ca tio n , A u d io v isu a l & C u ltu re E x ecu tiv e A gency

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SYNTHESIS OF AMPHOTERICIN B (K. C. NICOLAOU 1987). SYNTHESIS OF AMPHOTERICIN B (K. C. NICOLAOU 1987). RETROSYNTHESIS OF AMPHOTERICIN B ACCORDING TO K. C. NICOLAOU. RETROSYNTHESIS OF AMPHOTERICIN B. Threedifferent types of –OH protection. Trans double bond formation. - PowerPoint PPT Presentation

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Page 1: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

SYNTHESIS OF AMPHOTERICIN B (K. C. NICOLAOU 1987)SYNTHESIS OF AMPHOTERICIN B (K. C. NICOLAOU 1987)

I n ten siv e P ro g ram 31388-I C -11-2005-1-G R -E R A SM U S-I P U C -1

SY N A PS: Synthesis and R etrosynthesis in the C hem istry

o f N a t u r a l P r o d u c t s

N A T U R A L PR O D U C T C H E M I ST R Y

M o d u le 2

R etrosynthetic A pproaches T ow ards the Synthesis of N atural Pr oducts

P r o f. H . E . K ater in o p o u lo s

E d u catio n , A u d io v isu al & C u l tu re E xecu tiv e A gen cy

Page 2: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

SYNTHESIS OF AMPHOTERICIN B (K. C. NICOLAOU 1987)

SYNTHESIS OF AMPHOTERICIN B (K. C. NICOLAOU 1987)

Page 3: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

RETROSYNTHESIS OF AMPHOTERICIN B ACCORDING TO K. C. NICOLAOU

RETROSYNTHESIS OF AMPHOTERICIN B ACCORDING TO K. C. NICOLAOU

Page 4: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

RETROSYNTHESIS OF AMPHOTERICIN BRETROSYNTHESIS OF AMPHOTERICIN B

Threedifferent typesof –OH protection

Trans double bondformation

Page 5: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

THE HORNER-WADSWORTH-EMMONS OLEFINATION(Ketophosphonate-aldehyde condensation)

THE HORNER-WADSWORTH-EMMONS OLEFINATION(Ketophosphonate-aldehyde condensation)

JACS, 1961, 83, 1733-1738

Page 6: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

RETROSYNTHESIS OF AMPHOTERICIN BRETROSYNTHESIS OF AMPHOTERICIN B

Page 7: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

RETROSYNTHESIS OF AMPHOTERICIN BRETROSYNTHESIS OF AMPHOTERICIN B

These carbons are temporarily kept as protected alcohols

Page 8: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

RETROSYNTHESIS OF AMPHOTERICIN BRETROSYNTHESIS OF AMPHOTERICIN B

Page 9: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

Page 10: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

O OH

OH

OH

HO

O

OH

HO

O

O

O

OH

TBDPSiO

O

O

Page 11: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

O

OH

TBDPSiO

O

O

O

PhO(S)CO

TBDPSiO

O

O

O

H

TBDPSiO

O

O

Page 12: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

THE BARTON-McCOMBIE REACTION MECHANISMTHE BARTON-McCOMBIE REACTION MECHANISM

Page 13: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

OHCH=O

TBDPSiO

OH

Page 14: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

OH OH

TBDPSO

O O

TBDPSO

O O

TBDPSOHO

F-

O O

TBDPSOOBn

O O

OHOBn

Page 15: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

SYNTHESIS OF NORTH-EASTERN SECTION OF AMPHOTERICIN B

Page 16: SYNTHESIS OF AMPHOTERICIN B   (K. C. NICOLAOU 1987)
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