HOThe sequence below shows a synthesis of the alkaloid (+)-lentiginosine.N1PhHOHHN.NBr(EtO)₂P- CO₂MePhNaNx=H38Me₂S=ONEt3-78 °COSIMe₂ BuOSiMe₂ BuPPH3, NEt3HOSiMe₂ BuOSiMe₂¹Bu2Ph2 stepsPhCH₂O Ph-H OSiMe₂¹BuIOHOSIMe₂ BuOH(+)-lentiginosine-CO₂EtPhCH₂O2 stepsPPh3-78 °C Ph.Ph.H OHOHOSIMe₂ BuOSIMe₂ Bu(a) Draw a curved arrow mechanism for all of the following transformations. Whereappropriate, comment on any issues of chemo-, regio- or stereoselectivity that arise.(i) alcohol 1 → aldehyde 2(ii) aldehyde 2 → ester 3(iii) aldehyde 5 → alkene 6(iv) alcohol 7 →→ amine 8(b) Suggest reagents and conditions to achieve both of the following transformations.(i) alcohol 4 → silyl ether 5(ii) amine 8 → (+)-lentiginosine

The objective of this question is to synthesis of (+)-lentiginosin involves several steps. Due to…

HO The sequence below shows a synthesis of the alkaloid (+)-lentiginosine. N 1 Ph H OH HN- 7 & O CI O CI Me₂S=O NEt3 -78 °C OSIMe₂ Bu ▪OSiMe₂¹Bu NBr PPH3, NEt3 OSIM-BU 2 Ph H O 2 steps (EtO)₂P. PhCH₂O Ph CO₂Me Na ".. OH N Ph HOSiMe₂ Bu H 3 OSIMe₂ Bu -CO₂Et 2 steps O PhCH₂O -78 °C Ⓒ PPh3 Ph. Ph O O IHOH HOSiMe Bu O OH OSIMe₂ Bu 5

HO The sequence below shows a synthesis of the alkaloid (+)-lentiginosine. N 1 Ph H OH HN- 7 & O CI O CI Me₂S=O NEt3 -78 °C OSIMe₂ Bu ▪OSiMe₂¹Bu NBr PPH3, NEt3 OSIM-BU 2 Ph H O 2 steps (EtO)₂P. PhCH₂O Ph CO₂Me Na ".. OH N Ph HOSiMe₂ Bu H 3 OSIMe₂ Bu -CO₂Et 2 steps O PhCH₂O -78 °C Ⓒ PPh3 Ph. Ph O O IHOH HOSiMe Bu O OH OSIMe₂ Bu 5

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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