Answered step by step
Verified Expert Solution
Link Copied!

Question

1 Approved Answer

Provide a full mechanism, using the reagents/reaction conditions in the picture. Use curly arrow notation as appropriate. HO Me Me NaCIO, 78% 11 PMBO 1.

Provide a full mechanism, using the reagents/reaction conditions in the picture. Use curly arrow notation as appropriate.

HO Me Me NaCIO, 78% 11 PMBO 1. Ph3P+CHBr NaHMDS, 78% OTBDPS HO 2. TBSOTf 2,6-lutidine, 96% PMBO 3. TBAF, ACOH, 77% 1. (COCI)2, DMSO, Et3N 2. HSCHCHCHSH BF3*OEt 85% (2 steps) Me Me 13 OTBS Me Me S OTBDPS Sml2, PhCHO quant., d.r. >20:1 Me Me 16 9 OH 1. SO3 py, Et3N DMSO 2. NACIO OTBDPS PMBO PGO OH OPMB 88% (2 steps) PMBO 10 Me Me DIBALH, 95% OTBS tBuLi, HMPA, THF -78 to -50 C Me Me 76%, 88% based on recovered 9 OTBDPS 14: PG = Bz 8: PG = H COH 6 PMBO HG-II, CSA crotonaldehyde 77%, d.r. >20:1 HO PMBO S. Me Me OH MesN Cl... CI Ru Pr 12 Me Me HG-II CHO NMes OTBDPS OTBDPS 15 Scheme 2. Synthesis of carboxylic acid 6. CSA=10-camphorsulfonic acid, d.r.= diastereomer ratio, HMDS=hexamethyldisilazide, HMPA = hex- amethylphosphoramide, Mes=mesityl, py=pyridine, TBAF = tetra-n-butylammonium fluoride, Tf=trifluoromethanesulfonyl.

Step by Step Solution

3.42 Rating (146 Votes )

There are 3 Steps involved in it

Step: 1

The Arrow Notation in Mechanisms Since chemical reactions involve the b... blur-text-image

Get Instant Access to Expert-Tailored Solutions

See step-by-step solutions with expert insights and AI powered tools for academic success

Step: 2

blur-text-image

Step: 3

blur-text-image

Ace Your Homework with AI

Get the answers you need in no time with our AI-driven, step-by-step assistance

Get Started

Recommended Textbook for

Organic Chemistry

Authors: Marc Loudon

5th edition

981519431, 978-0981519449, 098151944X, 978-0-98151943, 978-0981519432

More Books

Students also viewed these Chemistry questions

Question

Describe Frederick Herzberg's hygiene theory of employee needs.

Answered: 1 week ago